Category: Automation & Cold Email

A cold email is a one-to-one message you send to someone who has never heard from you, with a specific reason to start a conversation. Done well, it books meetings and opens doors. Done badly, it burns your domain and lands every future email in spam. This guide covers the writing, the setup behind it, and 12 templates you can adapt today.

What Is Cold Email? The Meaning in Plain Terms

Cold email is unsolicited outreach to a person you have no existing relationship with. “Cold” means the recipient did not sign up, did not request contact and probably does not know your name.

Cold emailing is the practice of doing this deliberately and repeatedly, usually for business. Salespeople use it to book demos. Founders use it to reach investors. Freelancers use it to find clients. PR teams use it to pitch journalists and media outlets.

A real cold email is narrow. It goes to one person, or a small, carefully chosen list. It references something specific about them. It asks for one small action.

That is what separates it from spam. Spam is untargeted, often deceptive, and sent at volume to people who never had a reason to hear from you.

Cold email vs. email marketing vs. spam

People mix these up all the time. The difference matters because each one runs under different rules and on different tools.

	Cold email	Email marketing	Spam
Recipient opted in?	No	Yes	No
Typical volume	Dozens to hundreds per day	Thousands per send	As many as possible
Personalisation	Written for one person or segment	Segment-level	None or fake
Format	Plain text, short	Designed, often with images	Varies
Sent from	Real inbox (Google Workspace, Microsoft 365)	An ESP such as Mailchimp or Klaviyo	Anywhere
Goal	Start a conversation	Nurture and sell to subscribers	Trick or flood

Email marketing works with people who already gave you permission. Cold email is about earning the first reply. If you want the full picture of permission-based campaigns, our guide to what email marketing is and how it actually works covers that side.

One practical consequence: do not send cold email through your email service provider. Mainstream ESPs require opt-in lists in their acceptable use policies and will suspend accounts that send to people who never subscribed. Cold outreach goes out from real mailboxes, either by hand or through a cold email platform that connects to those mailboxes.

Is Cold Emailing Legal?

In most markets, yes, for B2B outreach, provided you follow the rules. The rules differ a lot by country, and “B2B” does not give you a free pass everywhere.

Region	Law	Consent needed for B2B cold email?	Key obligations	Maximum penalty
United States	CAN-SPAM Act	No (opt-out model)	Honest headers and subject, physical postal address, working opt-out, honour opt-outs within 10 business days	$53,088 per email (2025 FTC adjustment)
European Union	GDPR + national ePrivacy laws	Varies by country; many allow B2B under legitimate interest	Lawful basis, tell people where you got their data, honour objections	€20 million or 4% of global annual turnover
Germany	UWG §7 + GDPR	Generally yes, prior consent	Stricter than most EU states for email advertising	Varies; injunctions and fines
United Kingdom	UK GDPR + PECR	No for corporate addresses; yes for sole traders and some partnerships	Identify yourself, offer opt-out, lawful basis	Enforced by the ICO
Canada	CASL	Yes (express or implied)	Implied consent can apply if the address is conspicuously published and your message relates to their role	Up to CAD $10 million per violation

Two points get missed most often.

GDPR Article 14 applies to you. If you collected someone’s details from a source other than them, such as a company website or LinkedIn, you have to tell them where you got the data and how to object. A single line in the email or a link to your privacy notice handles this.

CAN-SPAM covers B2B email. There is no business exemption. Every commercial message needs a valid postal address and a clear way to opt out.

This is not legal advice. If you sell into Germany, Canada or a regulated industry, get a lawyer to review your approach once.

Set Up Your Sending Before You Write a Word

Most cold email fails at the infrastructure level. The copy never gets a chance because the message lands in spam or bounces. Fix this first.

Use a separate sending domain

Do not send cold outreach from your main company domain. If your cold campaigns pick up spam complaints, your invoices, password resets and customer emails suffer too.

Register a secondary domain that clearly belongs to your brand. If your company is acme.com, something like tryacme.com or acmehq.com works. Redirect the website to your main site so anyone who checks finds a real business. Never use a lookalike domain designed to impersonate someone else.

Authenticate the domain with SPF, DKIM and DMARC

Every sending domain needs all three records. Since February 2024, Gmail and Yahoo require them for bulk senders, and Microsoft started enforcing similar rules for Outlook.com in May 2025.

An SPF record for a Google Workspace domain looks like this:

Type: TXT
Host: @
Value: v=spf1 include:_spf.google.com ~all

For Microsoft 365, swap the include:

Type: TXT
Host: @
Value: v=spf1 include:spf.protection.outlook.com ~all

Only keep one SPF record per domain. If a cold email platform sends on your behalf through its own servers, add its include to the same record.

DKIM is generated inside your mail provider. In Google Workspace, go to Admin console > Apps > Google Workspace > Gmail > Authenticate email, generate a 2048-bit key, and publish it:

Type: TXT
Host: google._domainkey
Value: v=DKIM1; k=rsa; p=MIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEA...

Then return to the same screen and click Start authentication. Many people publish the record and forget this last click.

DMARC ties it together. Start with monitoring:

Type: TXT
Host: _dmarc
Value: v=DMARC1; p=none; rua=mailto:[email protected]

Once reports show your legitimate mail passing, move to p=quarantine. A policy of p=none meets the current Gmail, Yahoo and Microsoft minimum.

Know the mailbox provider rules

These are the rules your cold email lives under. Even if you never reach the bulk thresholds, meeting them is the baseline for decent inbox placement.

Provider	Effective date	Who it applies to	Requirements
Gmail (all senders)	February 1, 2024	Anyone sending to personal Gmail accounts	SPF or DKIM, valid forward and reverse DNS, TLS, spam rate below 0.3%
Gmail (bulk senders)	February 1, 2024, with phased enforcement through 2024	5,000+ messages per day to Gmail accounts	SPF and DKIM, DMARC (p=none minimum), From domain aligned with SPF or DKIM, one-click unsubscribe for marketing mail, unsubscribes processed within 2 days
Yahoo	February 2024	Bulk senders	SPF, DKIM, DMARC, one-click unsubscribe, honour unsubscribes within 2 days, low complaint rate
Microsoft (Outlook.com, Hotmail, Live)	May 5, 2025	5,000+ messages per day to Microsoft consumer domains	SPF, DKIM, DMARC (p=none minimum, aligned with SPF or DKIM)

Google’s guidance is to keep your spam rate under 0.1% and never let it reach 0.3%. With cold email, a few annoyed recipients clicking “Report spam” gets you there fast. That is the strongest argument for tight targeting.

Respect sending limits

Each mailbox has a hard cap. Free Gmail allows 500 recipients per day. Google Workspace allows 2,000 messages per user per day. Microsoft 365 allows 10,000 recipients per day and 30 messages per minute.

Those caps are ceilings, not targets. For cold outreach, we keep each inbox to roughly 30 to 50 new cold emails a day, and we add inboxes rather than pushing one harder. A brand-new domain should start lower and ramp up over two to four weeks.

If you connect your inbox to a sending platform over SMTP, use port 587 with STARTTLS unless the tool specifies otherwise. Our explainer on which SMTP port you should use covers the options.

How to Write a Cold Email That Gets a Reply

Every good cold email answers three questions within about five seconds. Who are you? Why me? What do you want?

Here is the anatomy, part by part.

Subject line

Write it like a colleague would. Short, lowercase-friendly, specific. Three to six words is plenty.

Good: “question about your Q3 hiring”, “idea for {Company}’s onboarding”, “{Mutual contact} suggested I reach out”.

Bad: “Quick question!!!”, “Partnership Opportunity”, “Re:” on a first email. That last one is deceptive and it falls foul of CAN-SPAM’s rule against misleading subject lines.

Opening line

Drop “I hope this email finds you well.” Everyone skips it, and it signals a template. Open with them instead: something they wrote, launched, hired for or said.

The first line also shows as preview text in most inboxes. Treat it as a second subject line.

Relevance

One or two sentences connecting their situation to a problem you solve. Be specific. “Companies like yours struggle with churn” says nothing. “You’ve opened four CS roles since March, which usually means onboarding is straining” shows you did the work.

The offer

What do you bring? Keep it to one result, ideally with a number from a real customer. Skip feature lists. Nobody reads them in a cold email.

Call to action

Ask for one small thing. “Worth a 15-minute call next week?” works better than a calendar link in a first email, because it asks for a reply rather than a commitment. Interest-based CTAs (“Is this on your radar?”) work well for senior people.

Sign-off and footer

Your name, title, company and one link at most. Add an opt-out line and your postal address to stay on the right side of CAN-SPAM. Something as simple as “Not relevant? Reply ‘no thanks’ and I won’t follow up” works for the opt-out.

Format rules

• Plain text. No images, logos or HTML designs.
• Under 125 words for the first email. Shorter is usually better.
• One link at most. Zero is often safer on new domains.
• Turn off open tracking. Tracking pixels are tiny images that can hurt deliverability, and Apple Mail Privacy Protection has inflated open rates since 2021 anyway, so the data is unreliable.
• No attachments. Offer to send assets after they reply.

How to Pick the Right Cold Email Template

Templates save time, but the wrong one wastes a good prospect. Use these criteria to choose.

How much do you know about them? If you found a real trigger, such as a funding round, new hire or product launch, use a trigger template. If all you have is a job title, you need more research, not a cleverer template.

What relationship exists already? A mutual contact, a shared event or a past touchpoint beats any pitch. Always use the warmest angle you have.

How senior are they? Executives respond to short, outcome-led notes. Managers respond to specifics about their daily work.

What do you want? A meeting, an introduction, a piece of feedback or a partnership each need a different ask.

What proof can you offer? If you have a strong case study from their industry, lead with it. If you don’t, lead with insight about their business instead.

Quick-Reference: 12 Cold Email Templates Compared

#	Template	Best use	Research needed	Ask size	Ideal length
1	Trigger-based opener	Sales, any industry	High	Small	60-90 words
2	Observation and idea	Agencies, consultants	High	Small	70-100 words
3	Right-person referral	Finding the decision maker	Low	Very small	40-60 words
4	Mutual connection	Any warm-ish lead	Medium	Small	50-80 words
5	Peer proof	Sales with strong case studies	Medium	Medium	70-100 words
6	Value-first share	Long sales cycles	Medium	Very small	60-80 words
7	Event follow-up	After conferences or webinars	Low	Small	50-80 words
8	New role congrats	Leaders in their first 90 days	Medium	Small	60-90 words
9	Partnership pitch	Co-marketing, integrations	High	Medium	80-120 words
10	Media pitch	PR, guest posts	High	Medium	80-120 words
11	Networking or job ask	Career outreach	Medium	Small	60-100 words
12	Breakup follow-up	Final touch in a sequence	None	Very small	30-50 words

12 Cold Email Templates, Ranked

These are ranked by how reliably each one starts real conversations across the widest range of situations. Replace everything in curly brackets. If you can’t fill a bracket with something true and specific, skip that prospect or pick a different template.

1. The Trigger-Based Opener (Top Pick)

This is our top pick because it forces you to have a reason for every email. A trigger is a recent, public event that makes your offer timely: funding, hiring, a launch, an expansion, a tech change.

Subject: {Trigger} at {Company}

Hi {First name},

Saw {Company} just {trigger, e.g. “opened a Berlin office”}. Teams expanding into new markets usually hit {specific problem} in the first few months.

We help {type of company} {result}. {Customer} cut {metric} by {number} after a similar move.

Worth a short call to see if it applies to you?

{Your name}

Why it works: The timing feels natural, and the problem is one they are likely facing right now. Good sources of triggers include company press pages, job boards, funding announcements and the prospect’s own posts.

2. The Observation and Idea

Best for agencies, consultants and anyone selling expertise. You point out something specific you noticed and offer one idea for free.

Subject: idea for {Company}’s {area}

Hi {First name},

I was looking at {specific asset, e.g. “your pricing page”} and noticed {observation}.

One quick idea: {specific, useful suggestion in one sentence}. We did something similar for {client} and saw {result}.

Happy to send over two or three more ideas if this is useful. Want them?

{Your name}

Why it works: You give before you ask. The CTA is tiny, and a reply costs them nothing. Make sure the observation is accurate. Getting their product wrong ends the relationship before it starts.

3. The Right-Person Referral

Use this when you know the company is a fit but can’t tell who owns the decision.

Subject: who handles {area} at {Company}?

Hi {First name},

I’m trying to reach whoever looks after {area} at {Company}. Is that you, or would someone else be better?

Short version: we help {type of company} {result}.

Thanks either way,

Why it works: It is easy to answer, and a referral from inside the company (“Emma suggested I reach out”) warms up your next email. Send it to someone adjacent to the decision, not to the CEO of a 2,000-person company.

4. The Mutual Connection

If you share a contact, lead with it. Ask the mutual contact first whether you can use their name.

Subject: {Mutual contact} suggested I reach out

Hi {First name},

{Mutual contact} mentioned you’re working on {project or goal}. We’ve been helping {similar company} with exactly that.

{One line on result.}

Would you be open to a 15-minute chat next week?

{Your name}

Why it works: Borrowed trust is the fastest way to warm a cold lead. Never name-drop someone without permission. It gets checked more often than you’d think.

5. The Peer Proof

Lead with a customer they know or respect, ideally a direct competitor or peer.

Subject: how {Peer company} {result}

Hi {First name},

{Peer company} was dealing with {problem}. After switching to {product}, they {specific result with number} in {timeframe}.

Given {Company}’s {similar situation}, I suspect you might see something similar.

Open to seeing how they did it?

{Your name}

Why it works: Social proof from a peer lowers perceived risk. Only use customer names and numbers you have permission to share.

6. The Value-First Share

For long sales cycles or senior buyers who won’t take a meeting from a stranger. You share useful content with no strings.

Subject: {topic} data you might find useful

Hi {First name},

We just pulled together {content, e.g. “a breakdown of how 40 SaaS companies price annual plans”}. Given {Company}’s {relevant context}, figured it might be useful.

Want me to send it over?

{Your name}

Why it works: Asking before sending keeps the first email link-free, which helps deliverability on newer domains. Make sure the content is genuinely good. Recycled blog posts won’t earn a second email.

7. The Event Follow-Up

Use within a week of a conference, webinar or meetup where they spoke or attended.

Subject: your talk at {Event}

Hi {First name},

Caught your session on {topic} at {Event}. Your point about {specific detail} stuck with me, especially {why}.

We work on {related problem} with {type of company}. Would be good to compare notes for 15 minutes if you’re open to it.

{Your name}

Why it works: A shared experience makes the email feel lukewarm rather than cold. Quote something specific so it’s obvious you were really there.

8. The New Role Congrats

New leaders usually have budget, a mandate to change things and a 90-day window to show results.

Subject: congrats on the new role

Hi {First name},

Congrats on joining {Company} as {title}. The first few months in a role like that usually mean {common priority}.

We’ve helped {number or names} of new {titles} {result} in their first quarter.

Worth a quick chat once you’ve settled in?

{Your name}

Why it works: The timing is right, and the CTA respects that they’re busy. Wait two to three weeks after the announcement so they’re not buried in congratulations.

9. The Partnership Pitch

For integrations, co-marketing, affiliate deals and joint content.

Subject: {Your company} x {Their company}?

Hi {First name},

I run {role} at {Your company}. We serve {audience}, which overlaps heavily with {Their company}’s customers.

Idea: {specific partnership, e.g. “a joint webinar on X” or “a native integration between our platforms”}. For context, {proof of reach or traction}.

Is this something you’d explore? Happy to send a one-page outline.

{Your name}

Why it works: It frames mutual gain early and offers a concrete next step. Our guide to email pitch examples for sales, PR and partnerships has more variations on this one.

10. The Media Pitch

For PR, podcast guest spots and expert commentary. Journalists get buried in pitches, so relevance is everything.

Subject: data on {topic they cover}

Hi {First name},

Read your piece on {recent article}. We have {new data, story or expert} that adds {angle} to it.

Headline finding: {one striking, verifiable fact}.

Happy to share the full data or set up a call with {expert}. Would that be useful for an upcoming story?

{Your name}

Why it works: You’re offering material for their next story, not asking for a favour. Never pitch a journalist something outside their beat.

11. The Networking or Job Ask

For career outreach, informational interviews and reaching hiring managers directly.

Subject: question about {team} at {Company}

Hi {First name},

I’m a {role} with {experience} and I’ve followed {Company}’s work on {specific thing} for a while.

Would you be open to 15 minutes to share how your team approaches {topic}? I’d value the perspective, and I’ll keep it to the time.

{Your name}

Why it works: Asking for insight gets far more replies than asking for a job. If the conversation goes well, the job question follows naturally.

12. The Breakup Follow-Up

The last email in a sequence. It closes the loop politely and often gets the highest reply rate of any follow-up.

Subject: closing the loop

Hi {First name},

I’ve reached out a few times about {topic} and haven’t heard back, so I’ll assume the timing isn’t right.

If that changes, just reply here. Wishing you a good quarter.

{Your name}

Why it works: It removes pressure and gives an easy out. Some people reply simply to say “not now, try in Q2,” which is valuable information.

How to Follow Up Without Being Annoying

Most replies come after the first email, not from it. A short sequence of three to four emails total is our working standard.

Email	Timing	Purpose
1	Day 1	Main pitch using one of the templates above
2	Day 3-4	Short bump in the same thread with one new detail
3	Day 8-10	New angle: a case study, a question or a useful resource
4	Day 15-20	Breakup email

Rules for follow-ups:

• Reply in the same thread so context stays visible.
• Add something new each time. “Just bumping this to the top of your inbox” adds nothing.
• Stop immediately when someone replies, books, opts out or bounces. Good cold email platforms do this automatically.
• Never follow up after a “no.” Remove them and move on.

If you’re sending manually, you can schedule emails in Gmail to land at the start of the recipient’s workday in their own time zone. That small detail helps more than most subject line tweaks.

Manual Sending vs. a Cold Email Platform

Below about 20 emails a day, sending by hand from Gmail or Outlook is fine. You’ll write better emails because each one gets your full attention.

Past that, a dedicated cold email platform makes sense. Look for these features:

• Multiple inbox support so you can spread volume across mailboxes and domains.
• Automatic stop-on-reply across every step in a sequence.
• Sending windows and throttling to space emails out like a human would.
• Plain-text sending with open tracking off by default, or easy to disable.
• CRM sync so replies and meetings land in your pipeline without manual entry.
• Bounce handling that removes bad addresses after the first hard bounce.

Avoid any tool that sells you contact data scraped without a lawful basis, or that encourages huge volumes from a single inbox. Those are shortcuts that end with a blocklisted domain.

Metrics to Watch

Opens are no longer a reliable signal, so focus on what happens after delivery. These are the thresholds we work to.

Metric	What it tells you	Where to check	Healthy range
Bounce rate	List quality	Your sending platform or inbox	Under 2%; pause and clean the list above that
Spam complaint rate	How recipients feel about you	Google Postmaster Tools, Yahoo Sender Hub	Under 0.1%; never reach 0.3% (Google’s limit)
Reply rate	Overall relevance	Sending platform	Track the trend by campaign
Positive reply rate	Real interest	Manual tagging or CRM	The number that matters most
Meetings booked	Business outcome	CRM or calendar	Measure per 100 prospects contacted

Treat reply rate as relative, not absolute. Compare one campaign against another, not against a figure from someone else’s industry. When you want to know which subject line or opener works better, run proper A/B testing with only one variable changed and enough sends on each side to mean something.

Google Postmaster Tools only shows data once you send meaningful volume to Gmail users, so small senders may see nothing there. In that case, watch for a sudden drop in replies. It’s often the first sign you’ve slipped into spam.

Common Cold Email Mistakes

Writing about yourself first. If the first two sentences are about your company, the reader has already gone. Open with them.

Faking personalisation. “I loved your recent post!” with no detail is worse than no personalisation at all. People can tell.

Asking for too much. A 45-minute demo request from a stranger rarely gets a yes. Ask for a reply, a short call or permission to send something.

Sending too fast on a new domain. Volume on day one is the most common reason new senders end up in spam. Ramp slowly.

Using HTML designs and images. Cold emails should look like a person typed them. Banners and logos make them look like campaigns, and filters treat them that way.

Ignoring opt-outs. Every “please remove me” must be honoured quickly and permanently, across every inbox and tool you use. CAN-SPAM gives you 10 business days. Gmail and Yahoo expect unsubscribes processed within 2 days for bulk senders. Aim for same-day.

Hiding where you found their data. Under GDPR, you owe recipients that information. A short line such as “I found your details on your company’s team page” handles it and builds trust.

FAQ

How to create a cold email?

Start with research: find one specific, recent reason to contact the person. Then write a short subject line, an opening line about them, one sentence on the problem you solve, one result as proof, and a single small ask. Keep it under 125 words, send it as plain text from an authenticated domain, and include an opt-out line and postal address.

What is the 60/40 rule in email?

It is an informal content guideline, not a formal standard, and different marketers define it slightly differently. The most common version says about 60% of your content should give value (insight, help, useful information) and 40% can promote your product or offers. In cold email, push it further: the first email should be almost entirely about the recipient’s situation, with only a line or two about you.

What are the 5 C’s of email?

The most widely used version is clear, concise, correct, courteous and complete. Some trainers swap in “compelling” or “conversational.” For cold email, concise and clear matter most: one idea, one ask, no jargon, and nothing the reader has to reread to understand.

What does “cold reach out” mean?

Cold reach out means contacting someone who has no prior relationship with you and hasn’t asked to hear from you. It can happen over email, LinkedIn or phone. Cold email is the most common form because it’s scalable, asynchronous and easy for the recipient to answer on their own time.

Is cold email the same as spam?

No. Cold email is targeted, honest and sent to people with a plausible reason to care. Spam is untargeted, often deceptive and sent at volume. The line is crossed when you mislead people, ignore opt-outs, use bought lists or send to people with no connection to your offer.

How many cold emails can I send per day?

Hard limits are 500 recipients per day for free Gmail, 2,000 messages and 10,000 total recipients per day per Google Workspace user, and 10,000 recipients per day on Microsoft 365 business plans (consumer Outlook.com accounts are capped at 5,000 recipients per day). For cold outreach, stay far below those. We recommend 30 to 50 new cold emails per inbox per day, after a warm-up period of two to four weeks on a new domain.

A strong email pitch is usually under 150 words. It opens with something specific to the recipient, offers one clear piece of value and ends with one easy ask. Below are 14 email pitch examples for sales prospects, journalists and potential partners, with notes on why each works and when to use it. After the examples you’ll find follow-up timing, the deliverability setup and the legal rules that decide whether anyone reads your pitch.

The four parts every pitch needs

Every pitch that gets a reply has the same skeleton, whatever the context. Strip away the tone and the industry jargon and you’ll find four parts.

1. The hook. The first line proves you know who they are. It could be a recent article, a new job posting, a product launch or a mutual connection. A generic compliment doesn’t count.
2. The bridge. One or two sentences that connect their world to yours. This answers “why are you emailing me, and why now?”
3. The value. What they get. For a prospect, that’s a result. For a journalist, it’s a story their readers will care about. For a partner, it’s access to an audience or a product gap filled.
4. The ask. One action, small enough to say yes to in ten seconds. “Worth a 15-minute call Thursday?” works better than “Let me know your thoughts.”

The weight of each part shifts by pitch type. Sales prospects care about their problem, reporters care about their readers, and partners care about the trade. The table below shows the working ranges I use. They come from practice, not from a survey.

	Sales pitch	PR / media pitch	Partnership pitch
Question in the reader’s head	Does this fix a problem I have?	Will my audience care?	What do we each get?
Strongest hook	Trigger event, peer result	Fresh data, exclusive, timely angle	Audience overlap, complementary product
Working length	50-125 words	100-200 words	100-150 words
Best ask	Short call or yes/no question	“Want the full data?”	Short call or a specific proposal
Follow-ups	2-3 over two to three weeks	1, three to five days later	1-2 over two weeks

What 12 million outreach emails tell you

The most useful public dataset on cold pitching is still the analysis Backlinko ran with outreach platform Pitchbox. It looked at 12 million outreach emails and was published in 2019. That makes it old, and inboxes have only grown more crowded since, so treat the response rate as a ceiling rather than a target. The relative findings still match what most outreach teams see today.

Finding (Backlinko and Pitchbox, 12M emails, 2019)	Result
Average response rate across all outreach	8.5%
Personalized subject line vs none	30.5% higher response rate
Personalized message body vs none	32.7% higher response rate
Sending at least one follow-up	65.8% more responses
Contacting multiple people at the same organization	93% higher response rate
Subject line length with the best response rate	36-50 characters

Two things stand out. First, more than 90% of cold pitches get no reply at all, so silence is the default rather than a verdict on you. Second, the biggest lifts come from things that take effort: personalizing, following up and finding the right second contact. No template does that part for you.

Find the angle before you write a word

Most bad pitches fail before the first sentence because the sender never found an angle. They had a product or a press release and went looking for people to send it to. Flip that order.

Three rules for getting replies

• Relevance beats volume. Ten pitches to people who have written about, bought or partnered on exactly your thing will outperform 500 to a loosely related list. Every annual journalist survey from Cision and Muck Rack puts irrelevant pitches at the top of reporters’ complaints.
• Give before you ask. Lead with a data point, a fix, a quote or an introduction they can use even if they ignore the rest of the email.
• Make yes easy. One ask, one time slot, one attachment at most. Every extra decision you hand someone lowers the chance they make any of them.

Where good angles come from

Good angles come from a handful of reliable places. Recent work is one: an article they wrote, a podcast they appeared on, a feature their product shipped. Trigger events are another, such as funding rounds, new leadership, hiring sprees, expansions and pricing changes.

Your own data counts too: customer results, survey findings and usage patterns nobody else has. So do gaps, meaning a story their competitor covered and they didn’t, or a product category their customers keep asking for.

If you can’t name the angle in one sentence, you aren’t ready to send.

Subject lines that get opened

The subject line has one job: get the email opened by the person it was written for. It shouldn’t sell, explain or tease. It should signal relevance.

Subject lines that tend to work:

• Your piece on four-day weeks (references their work)
• Data: 61% of freelancers raised rates in Q1 (leads with the hook for a reporter)
• Northwind + Fieldstack webinar idea (partnership, both names)
• Broken link on your pricing page (useful, specific, hard to ignore)
• Question about your SDR hiring (short, personal, curious)

Subject lines that get deleted:

• Quick question (every cold emailer uses it)
• Partnership opportunity!! (vague and shouty)
• Re: our conversation when there was no conversation (deceptive, and a CAN-SPAM problem)
• PRESS RELEASE: Company X Announces... (reads like a wire dump)

Sales email pitch examples

Company names, people and figures in every example below are placeholders. Swap in your own verified numbers. A pitch with an invented result is worse than one with no result at all.

Example 1: The trigger event pitch

When to use it: The prospect just did something public that creates a problem you solve, like hiring, raising money or launching in a new market.

Subject: Your six new SDR roles

Hi Priya,

Saw Northwind is hiring six SDRs this quarter. Congrats on the growth.

When outbound teams double in size, ramp time usually becomes the bottleneck. Fieldstack, a 40-person sales team in a similar spot, used Lumen Coach to cut new-rep ramp from 14 weeks to 9.

Worth a 15-minute look before your new hires start? I’m free Thursday at 11 or 2 your time.

Sam

Why it works: The opening line could only have been written to Priya. The bridge names the problem her hiring creates before she has felt it, and the proof comes from a comparable company. The ask offers two specific times, so replying takes one word.

Example 2: The “results” email

When to use it: You have a strong case study from a customer the prospect will recognize or relate to.

Subject: How Brightline cut refund requests by 22%

Hi Marcus,

You and Brightline sell into the same mid-market retail buyers, so this might be useful.

Their support team was handling about 900 refund requests a month. After adding our pre-purchase sizing quiz, that dropped 22% in one quarter, and the quiz paid for itself in the first month.

I put the before-and-after numbers on a single page. Want me to send it over?

Dana

Why it works: It leads with the result in the subject line, which is the only thing a busy buyer wants to know. The ask is a yes/no question about receiving a document rather than booking a meeting. That’s a smaller step and a natural opening for a reply.

Example 3: The relevant share email

When to use it: Early in a relationship, or with a prospect who isn’t ready to buy, to build familiarity without pushing.

Subject: Benchmark for your onboarding emails

Hi Leah,

I noticed Copperleaf just rebuilt its welcome sequence. It looks sharp.

We recently pulled activation data from 140 SaaS onboarding flows and found that the second email, not the first, drives most trial-to-paid conversions. The full breakdown is in a short PDF. No form, no gate.

Happy to send it if it’s useful. No pitch attached.

Owen

Why it works: It delivers something useful with no strings, and the observation proves Owen looked. Some prospects will reply just to get the PDF, which opens a conversation on your terms. Use this one sparingly. Three “no pitch attached” emails in a row and the reader stops believing you.

Example 4: The typo email

When to use it: You spotted a genuine error on the prospect’s site, app or emails, ideally one related to what you sell.

The typo email has been a staple of link-building outreach for years, and it works just as well in sales. You hand someone a fix before you ask for anything.

Subject: Broken link on your pricing page

Hi Tomas,

Quick heads-up: the “Compare plans” button on your pricing page returns a 404 on mobile Safari. I checked twice this morning.

I only noticed because I was looking at how SaaS teams handle plan comparison. We build pricing page tests for companies like yours, and broken mobile CTAs are the most common leak we find.

Either way, worth fixing today. If you’d like a free audit of the rest of the page, just reply “audit.”

Rina

Why it works: The first paragraph has value with no conditions attached. The pitch is one sentence and naturally connected to the problem. The ask is a one-word reply.

Be accurate. Point out an error that isn’t real, or one they’ve already fixed, and you look careless rather than helpful.

Example 5: The breakup follow-up

When to use it: As the final email in a sequence, after two or three unanswered attempts.

Subject: Closing the loop

Hi Priya,

I’ve reached out a couple of times about ramp time for your new SDRs and haven’t heard back, which usually means the timing’s wrong.

I’ll stop emailing about this. If onboarding becomes a priority later in the year, reply to this thread and I’ll pick it up from there.

Thanks either way,
Sam

Why it works: It’s honest, it removes pressure and it gives a clear exit. Breakup emails often get more replies than the emails before them, because people answer to say “not now, try in Q3.” That’s a useful answer. Stick to your word afterward. A breakup email followed by another pitch next week burns the relationship.

PR and media pitch examples

Journalists get far more pitches than they can read, so the rules tighten. Put the story in the first two lines. Paste the key facts into the email body instead of attaching them. Never pitch a reporter something outside their beat.

Example 6: The story pitch

When to use it: You have a human story with a clear arc, a tension and a person willing to talk on the record.

Subject: Bakery that moved to a 4-day week and grew 30%

Hi Jordan,

Your piece on the four-day week pilots got a lot of people in our town talking, including the owner of Crumb & Co.

Ellie Park moved her 18 staff to four-day weeks last spring, expecting to lose money. Instead, revenue grew 30% year over year and she hasn’t lost an employee since. She’s candid about what went wrong in the first two months too, including a rota disaster that nearly ended the experiment.

Ellie’s available for an interview this week and can share her monthly numbers. Would this fit something you’re working on?

Mia Chen
Communications, Crumb & Co.

Why it works: It ties the pitch to the reporter’s own coverage, and the story has tension: she expected failure. It also offers something the reporter needs, an on-record source with real numbers and a willingness to talk about mistakes. Polished success stories are dull. Admitted struggles are a story.

Example 7: The exclusive research email

When to use it: You’ve commissioned a survey or have proprietary data, and you want one strong placement before wide release.

Subject: Exclusive: 61% of freelancers raised rates in Q1

Hi Sofia,

You’ve covered freelance pay more closely than anyone on the beat, so I wanted to offer you this first.

We surveyed 1,200 US freelancers in March. Three findings stood out:

• 61% raised their rates in Q1, up from 38% a year earlier
• Designers raised rates most often; writers least
• 1 in 4 now require a deposit before starting work

I can offer this to you exclusively until 9 a.m. ET on May 14, with the full dataset and methodology. Interested?

Raj

Why it works: The headline finding sits in the subject line. The bullets let the reporter judge the story in five seconds. The exclusive has a clear deadline, so she knows what she’s being offered and when it expires.

If she passes, honor the exclusive window before you take the data to anyone else. Methodology matters as well. Have sample size, dates and how respondents were recruited ready to send, because serious reporters will ask.

Example 8: The related story email

When to use it: A reporter covered a topic recently, and you have a genuine follow-up angle, new development or missing perspective.

Subject: Follow-up to your EV charger piece

Hi Andre,

Your story last month on broken public EV chargers named reliability as the top complaint. We track uptime across 4,000 chargers in the Northeast, and our April numbers suggest the problem is concentrated in a small set of hardware models rather than spread across the network.

I can share the model-by-model breakdown and put you in touch with our head of field operations, who’s happy to go on record.

Would a follow-up angle on this be useful?

Kate

Why it works: It doesn’t ask the reporter to start from scratch. It extends a story he already owns and offers a narrower, more surprising angle. Reporters like follow-ups because their editor already approved the topic once.

A second version of this pitch works when a reporter covered your competitor. “You wrote about X’s approach; here’s a company doing the opposite, with different results” is a legitimate angle, provided you can back the difference with numbers.

Example 9: The infographic email

When to use it: You’ve turned data into a clear visual and want editors, bloggers or newsletter writers to use it.

Subject: Chart for your remote work roundup

Hi Grace,

Your weekly remote work roundup regularly includes a “chart of the week,” so I thought this one might fit.

We mapped average home-office spending by country from our 2,000-customer dataset. The gap between Germany and the US surprised even us. A preview is pasted below, and the full-size chart and source CSV are free to use with credit.

[chart preview pasted inline]

Want the files?

Leo

Why it works: It targets a specific recurring slot in Grace’s newsletter, which shows research. The visual is in the body rather than hidden behind an attachment, and the source data is offered upfront, which matters to any editor who checks numbers.

Keep the inline image small. A large image with little text is a classic spam-filter signal, and many corporate mail systems block images by default.

Example 10: The expert commentary email

When to use it: A big news story just broke, and you have a credible expert who can add something reporters don’t already have.

Subject: Source on today’s Gmail spam rule change

Hi Nadia,

If you’re covering today’s Gmail sender announcement, our deliverability lead, Chris Okafor, has audited authentication for 300+ brands and can explain what changes for small senders.

One line you’re welcome to use: “Most small businesses already pass SPF. The ones who’ll get hurt are those who never set up DMARC and don’t know who’s sending email in their name.”

Chris is available by phone until 6 p.m. ET today.

Ben

Why it works: Speed and a usable quote. Reporters on deadline need sources who can talk now. A strong, quotable line in the email itself often gets used even without a call. Only send this when your expert truly has standing on the topic. Newsjacking with a weak source annoys reporters and gets you remembered for the wrong reasons.

Partnership pitch examples

Partnership pitches are closer to negotiations than requests. Both sides need to see the trade quickly, and the trade has to be roughly even. If the email reads like you want their audience for free, it’s dead.

Example 11: The co-marketing webinar pitch

Subject: Northwind + Fieldstack webinar idea

Hi Elena,

Our customers keep asking how to connect their CRM data to onboarding emails, and Fieldstack is the integration we recommend most often.

Idea: a 45-minute joint webinar in June, “From signed deal to activated customer,” with one speaker from each side. We’d handle production and promotion to our 22,000 subscribers. You’d promote to yours, and both teams get the full registrant list.

If that’s interesting, I can send a one-page outline. Does a quick call next week work?

James

Why it works: It starts from a real overlap, shared customers, and names a specific format, date and title. That saves Elena from having to invent the idea herself. Spelling out who does what and who gets the leads answers her biggest question before she asks it.

Check consent before you promise registrant lists. Under GDPR in particular, sharing leads between companies needs a clear basis, usually stated on the registration form.

Example 12: The integration partnership pitch

Subject: 140 of your customers already use us

Hi Arjun,

We looked at our customer base and found 140 accounts that also use Ledgerly. Most of them export invoices to CSV and re-upload them into our dashboard every week.

A native integration would kill that step. We’ve scoped it at roughly six weeks of work on our side using your public API. We’d just need a sandbox account and a technical contact for questions.

Would you be open to listing it in your marketplace once it’s live? Happy to share the scope doc.

Wen

Why it works: It opens with a number that matters to Arjun, his own customers, and it shows the pain they’re living with. Then it lowers the effort on his side to almost nothing. Partners say yes to integrations that make their product stickier and cost them little.

Example 13: The newsletter sponsorship or creator pitch

Subject: Sponsoring your April issues

Hi Theo,

I’ve read your newsletter on indie SaaS pricing for about a year. Your teardown of usage-based plans is still pinned in our team channel.

We’d like to sponsor two issues in April. We make billing software for small SaaS teams, which seems a natural fit for your readers, and we’re happy to follow your usual format and disclosure rules.

Could you send your current rates and open dates?

Ana

Why it works: It’s direct. Creators get plenty of vague “let’s collaborate” emails, and one that says “we want to pay you, here’s when” stands out. Respecting their format and disclosure rules signals you won’t be a difficult sponsor. In the US, the FTC expects paid placements to be clearly disclosed, so a sponsor who mentions it upfront is easier to work with.

Example 14: The guest content or newsletter swap pitch

Subject: Content swap for May?

Hi Carla,

Your readers are mostly freelance designers and ours are mostly freelance developers. Both lists keep asking how to work together without scope creep.

Proposal: I write a piece for your blog on “how to brief a developer,” and you write one for ours on “how to brief a designer.” Each about 1,200 words, each linking back to the author’s site. We’d also feature yours in our newsletter, which goes to 9,000 subscribers.

Here are two posts I’ve written recently, so you can judge the fit: [titles pasted]

Interested?

Rob

Why it works: The trade is symmetrical and spelled out in two sentences. The topic idea already fits both audiences, and including writing samples answers the quality question before it’s raised.

Before and after: rewriting a weak pitch

Here’s a pitch that looks like thousands sent every day.

Subject: Partnership opportunity

Hi there,

I hope this email finds you well! My name is Jake and I’m the founder of Taskwise, an innovative AI-powered productivity platform that is revolutionizing the way teams work. We’ve been featured in several publications and have a growing user base.

I came across your website and think there could be some great synergies between our companies. We’d love to explore potential partnership opportunities, whether that’s co-marketing, integrations or something else.

Let me know if you’d be open to a call to discuss!

Best,
Jake

What’s wrong with it:

• “Hi there” tells the reader it went to a list.
• The first two sentences are about Jake, not the recipient.
• “Innovative,” “revolutionizing” and “synergies” carry no information.
• “Partnership opportunities… or something else” means Jake hasn’t done the thinking.
• The ask is a call with no agenda, which is a big commitment for zero clarity.

Here’s the rewrite.

Subject: Taskwise + Plannly: shared calendar sync

Hi Ruth,

Your changelog last week mentioned that calendar sync is the top request on your roadmap board. About a third of our 6,000 users also use Plannly, and they ask us for the same thing.

We’ve already built two-way sync with Google and Outlook calendars. We could expose it to Plannly through a lightweight integration, with no engineering needed on your end beyond OAuth approval.

Would a 20-minute walkthrough next Tuesday or Wednesday be useful?

Jake

The rewrite is about the same length. Every sentence now carries information, the opening is about Ruth’s roadmap, and the proposal is specific enough to say yes or no to.

Following up without being annoying

The Backlinko data shows at least one follow-up lifts responses by nearly two-thirds. Most replies to cold outreach still come from the first email, and each follow-up brings in fewer, but those later replies come from people who saw your pitch, meant to reply and forgot.

A cadence that works for most sales pitches:

Email	Timing	What it does
1. Pitch	Day 0	Full hook, value, ask
2. Nudge	Day 3-4	Reply in the same thread, one or two lines, a new detail
3. Value add	Day 8-10	Share a relevant resource or result
4. Breakup	Day 15-20	Close the loop politely (Example 5)

For journalists, one follow-up is the norm. Send it three to five days later and only if you have something to add, like a new data point, a confirmed interview slot or a timely news peg. “Just checking you saw this” adds nothing. A reporter who wanted it would have replied.

For partnerships, one or two follow-ups over two weeks is fine. If you have a mutual connection, the second follow-up is the moment to ask them for a warm intro instead.

A follow-up that adds something:

Hi Elena,

One addition to my webinar note: we just confirmed our VP of Customer Success as a speaker. She ran onboarding at a 2,000-seat rollout last year and has some good stories. Still keen if June works for your team.

James

Always reply in the same thread so the original pitch stays visible. And keep your sign-off consistent. A clean signature with name, role, company and one way to reach you looks more credible than a banner ad. If yours needs work, our email signature examples are a good place to steal from.

Get your pitches into the inbox

The best pitch in the world does nothing in a spam folder. Cold pitches are risky for deliverability because recipients haven’t asked for your email, and mailbox providers judge you on how people react.

Send from your own authenticated domain

Pitching from a free Gmail or Outlook address looks amateur to journalists and buyers, and you can’t authenticate it properly. Set up domain email on your company’s own address first. Then publish the three authentication records Gmail, Yahoo and Microsoft check.

An SPF record for a domain that sends through Google Workspace looks like this. If you send through other services too, add their include statements to the same single record.

example.com.  TXT  "v=spf1 include:_spf.google.com ~all"

DKIM is a public key published at a selector your provider names. In Google Workspace, you generate it under Admin console > Apps > Google Workspace > Gmail > Authenticate email.

google._domainkey.example.com.  TXT  "v=DKIM1; k=rsa; p=MIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEA..."

A starter DMARC record monitors without blocking anything and sends aggregate reports to an address you control:

_dmarc.example.com.  TXT  "v=DMARC1; p=none; rua=mailto:[email protected]"

Once reports show all your legitimate mail passing, move to p=quarantine and then p=reject to stop others spoofing your domain.

The sender rules you’re working under

Provider	Effective date	Rules that matter for pitching
Gmail (all senders)	February 1, 2024	SPF or DKIM, valid forward and reverse DNS, TLS, spam rate kept below 0.3% (Google advises under 0.1%)
Gmail (5,000+ messages a day to Gmail accounts)	February 1, 2024, with one-click unsubscribe required from June 1, 2024	SPF, DKIM and DMARC (p=none minimum), From domain aligned with SPF or DKIM, one-click unsubscribe on marketing mail
Yahoo (bulk senders)	February 2024	SPF, DKIM, DMARC, spam rate below 0.3%, one-click unsubscribe, unsubscribes honored within 2 days
Microsoft Outlook.com, Hotmail, Live (5,000+ messages a day)	May 5, 2025	SPF, DKIM and DMARC (p=none minimum) aligned with SPF or DKIM; non-compliant mail first routed to Junk, with rejection to follow

Most individual pitching never reaches 5,000 messages a day. Meet the bulk-sender rules anyway. Authentication costs nothing, and a single spam complaint from a cold pitch counts against you whatever your volume.

Keep volume human

Mailbox providers also cap how much one account can send. Google lists 500 messages a day for a free Gmail account and 2,000 per user for paid Google Workspace (limits as published by Google in 2025, lower during trials). Microsoft 365 caps most mailboxes at 10,000 recipients a day. Stay far below those. Pitching is a one-to-one activity, and 20 to 50 carefully researched emails a day is a sensible ceiling for a single sender.

Don’t run cold pitches through your newsletter tool either. Most small business email platforms, Mailchimp included, prohibit sending to contacts who haven’t opted in, and they will suspend your account for it.

High-volume sales teams often send outreach from a subdomain, such as mail.example.com, so a bad campaign doesn’t drag down the main domain. That’s reasonable for sales. For PR and partnership pitches, send from a real person’s mailbox on your main domain. A reporter who sees an unfamiliar lookalike domain has every reason to be suspicious.

The legal rules for cold pitches

Cold email is legal in many places when done right, but the rules vary by where the recipient is. A media pitch about genuine news is arguably not “commercial” under some laws. Sales and partnership pitches clearly are. The safe approach is to treat every pitch as if the rules apply.

Law	Where	What it requires for cold B2B pitches	Penalties
CAN-SPAM Act	United States	Accurate From and subject lines, your physical postal address, a clear way to opt out, opt-outs honored within 10 business days; applies to B2B email too	Up to $53,088 per violating email (FTC’s January 2025 inflation adjustment)
GDPR	EU and UK	A lawful basis (legitimate interest is common for B2B), telling people where you got their data, honoring objections promptly	Up to €20 million or 4% of global annual turnover (UK: £17.5 million)
PECR / national ePrivacy rules	UK and EU member states	UK allows cold email to corporate addresses with an opt-out; sole traders and individuals need consent. Several EU countries, including Germany, are much stricter	Set by national regulators
CASL	Canada	Consent required; implied consent can apply when an address is conspicuously published, carries no “no unsolicited email” notice and your message is relevant to the person’s role. Identify yourself and include an unsubscribe	Up to C$10 million per violation for businesses

This isn’t legal advice. For any outreach program beyond a handful of personal pitches, have a lawyer review your process for the countries you target. A short line at the bottom of sales pitches costs you nothing and keeps you on the right side of most of these rules. “Not relevant? Reply ‘no thanks’ and I won’t email again” works well.

Metrics worth tracking

Open rates are a weak signal for pitches. Apple Mail Privacy Protection, launched with iOS 15 in September 2021, preloads tracking pixels and inflates opens. Tracking pixels can also hurt deliverability on low-volume cold email. Many experienced outreach teams turn open tracking off entirely. Watch these instead:

• Reply rate: replies divided by delivered emails. Compare it to the 8.5% Backlinko average with caution, since that data is from 2019.
• Positive reply rate: replies that move things forward, such as a meeting, an interview or a “send me the data.” This is the number that matters.
• Outcome rate: meetings booked, articles published, partnerships signed per 100 pitches.
• Bounce rate: keep it under 2%. Above that, your list research needs fixing.
• Spam complaint rate: check Google Postmaster Tools if you send enough volume to see data, and keep it under 0.1%.

Review results by pitch type and angle, not just in aggregate. You’ll usually find one angle, often the trigger event or exclusive data pitch, outperforming everything else by a wide margin. Double down on it.

FAQ

What is an email pitch?

An email pitch is a short, personalized message asking someone to take one specific action. That might be a sales meeting, press coverage or a partnership. It differs from a newsletter or announcement because it’s written for one recipient and built around a reason they in particular should care.

How long should a pitch email be?

Aim for 75 to 150 words for sales and partnership pitches, and up to about 200 words for a media pitch that includes data. If the recipient has to scroll on a phone, it’s too long. Move detail into a follow-up or a one-page document they can request.

What are good email pitching examples for beginners?

Start with the typo email (Example 4) and the related story email (Example 8). Both are built on something you can verify, a real error or a real article. You don’t need a big brand or impressive results to make them work, only careful research.

How many follow-ups should I send?

For sales, two or three follow-ups over two to three weeks, ending with a breakup email. For journalists, one follow-up after three to five days, and only with new information. Stop immediately if anyone asks you to.

Should I attach a press release or pitch deck?

No, at least not in the first email. Attachments from unknown senders trigger spam filters, and many recipients won’t open them for security reasons. Paste the key facts into the body and offer the full document if they’re interested.

When is the best time to send a pitch?

Send during the recipient’s working hours, early in their week, and avoid Friday afternoons and holidays. For journalists, morning sends tend to fit editorial planning better than late-day pitches. Timing matters much less than relevance, though. A well-aimed pitch sent at a bad time beats a generic one sent at the perfect minute.

Use port 587 with STARTTLS for sending email from an app, website or mail client. Port 465 with implicit TLS is just as good if your provider supports it. Port 25 is the default SMTP port, but it is meant for server-to-server relay and is often blocked on home and cloud networks.

Quick SMTP port reference

Here is every SMTP port number you will run into, and what each is actually for.

Port	Encryption	Main use	Recommended?
25	None or opportunistic STARTTLS	Server-to-server relay (MTA to MTA)	Only for mail servers
587	STARTTLS (upgrade after connecting)	Authenticated message submission	Yes, the safe default
465	Implicit TLS (encrypted from the start)	Authenticated message submission	Yes, if supported
2525	Usually STARTTLS	Unofficial alternative to 587	Fallback only

What an SMTP port actually is

SMTP (Simple Mail Transfer Protocol) is the protocol that sends mail. A port is the numbered “door” on a server that a connection knocks on. Your mail client, website plugin or app needs both the server hostname and the right port to hand off a message.

SMTP only handles sending. Receiving and reading mail uses IMAP or POP3, which have their own ports (covered below).

Port 25: the original default SMTP port

Port 25 is the default port for SMTP, defined back in the early 1980s. It is still how mail servers pass messages to each other across the internet. When Gmail delivers a message to a company’s mail server, it connects on port 25.

The problem is that port 25 became the favourite of spam botnets. Infected home computers could connect directly to any mail server and blast junk. So many ISPs now block outbound port 25 on residential connections. Major cloud providers do too. Google Cloud blocks outbound port 25 to external addresses, and AWS restricts it on EC2 until you request removal.

That is a big part of how e-mail spam filtering works: the sending IP’s reputation matters as much as the message itself.

Port 587: your best bet for sending

Port 587 is the official message submission port (RFC 6409). It exists so that clients and apps can hand mail to their own provider, with a login, separate from server-to-server relay on port 25.

The connection starts in plain text. The client then issues the STARTTLS command, and the session upgrades to an encrypted one before your password is sent. Every major provider supports it, and ISPs rarely block it.

If you only remember one SMTP port, make it 587.

Port 465: SMTP over SSL/TLS

Port 465 has a messy history. It was assigned for SMTPS in the late 1990s, then revoked, but providers kept using it anyway. In 2018, RFC 8314 officially brought it back for message submission using implicit TLS.

Implicit TLS means the connection is encrypted from the first byte. There is no plain-text phase and no upgrade step. RFC 8314 actually prefers this approach over STARTTLS, because a STARTTLS upgrade can in theory be stripped by an attacker on the network.

In practice, both 465 and 587 are secure when configured correctly. Pick whichever your provider documents first.

Port 2525: the unofficial fallback

Port 2525 is not registered with IANA for SMTP. Transactional email services offer it anyway because some hosting companies block 25, 465 and even 587. If your server cannot reach your email service on standard ports, 2525 often gets through.

Email service	SMTP host	Supported ports
SendGrid	smtp.sendgrid.net	25, 587, 2525 (STARTTLS); 465 (TLS)
Mailgun	smtp.mailgun.org	25, 587, 2525 (STARTTLS); 465 (TLS)
Amazon SES	email-smtp.[region].amazonaws.com	25, 587, 2587 (STARTTLS); 465, 2465 (TLS)

Many small business email platforms hide these settings entirely and give you an API or plugin instead. If you are only doing email marketing through a hosted tool, you may never touch an SMTP port at all.

SMTP server and port for Gmail, Outlook and other providers

These are the common SMTP mail port settings for the big mailbox providers.

Provider	SMTP server	Port	Encryption
Gmail / Google Workspace	smtp.gmail.com	587 or 465	STARTTLS / SSL
Outlook.com / Hotmail	smtp-mail.outlook.com	587	STARTTLS
Microsoft 365	smtp.office365.com	587	STARTTLS
Yahoo Mail	smtp.mail.yahoo.com	465 or 587	SSL / STARTTLS
iCloud Mail	smtp.mail.me.com	587	STARTTLS
Zoho Mail	smtp.zoho.com	465 or 587	SSL / STARTTLS

Your normal account password usually will not work here. Gmail, Yahoo and iCloud expect an app password, which requires two-step verification, or an OAuth sign-in. Microsoft is retiring basic password authentication for SMTP, so plan on OAuth or an app password for Outlook and Microsoft 365 too.

SMTP, IMAP and POP3 ports

Setting up a mail client means entering both incoming and outgoing servers. Here is the full email port list.

Protocol	Job	Plain / STARTTLS port	Implicit TLS port
SMTP	Sending mail	587 (25 for relay)	465
IMAP	Reading mail, synced to server	143	993
POP3	Downloading mail to one device	110	995

For incoming mail, use 993 for IMAP or 995 for POP3. The unencrypted variants are rarely needed today.

How to choose the right SMTP port

Only use port 25 if you run a mail server that relays to other mail servers. Apps, websites and mail clients should never need it.

How to tell if an SMTP port is blocked

Test the connection before you blame your password. On macOS or Linux, open a terminal and run:

nc -vz smtp.gmail.com 587

On Windows, use PowerShell:

Test-NetConnection smtp.gmail.com -Port 587

A “succeeded” or “TcpTestSucceeded : True” result means the port is open. A timeout means something between you and the server is blocking it.

To confirm encryption actually works, use OpenSSL. For port 587:

openssl s_client -starttls smtp -connect smtp.gmail.com:587

For port 465:

openssl s_client -connect smtp.gmail.com:465

You should see a certificate chain and a 220 greeting from the server. If the port is blocked, contact your ISP or hosting company. Most will unblock 587 on request. Very few will open port 25 for residential customers.

Common mistakes when setting the SMTP port

Most “can’t send mail” tickets come down to a handful of errors:

• Encryption mismatch. Choosing SSL on port 587 or STARTTLS on port 465. The client hangs, then times out. Match 587 with STARTTLS and 465 with SSL/TLS.
• Using port 25 from an app. It gets blocked or lands in spam. Use 587.
• Account password instead of an app password. You will see an authentication error like 535. Generate an app password.
• Wrong hostname. smtp.office365.com and smtp-mail.outlook.com are not interchangeable for every account type.
• Local firewall or antivirus. Some security suites intercept outgoing mail connections. Temporarily disable the email scanning feature to test.
• No authentication enabled. Port 587 and 465 expect a username and password. Without them, the server rejects the message.

Correct ports get mail out of your app. They do not guarantee inbox placement. That still depends on SPF, DKIM and DMARC records for your sending domain.

FAQ

How to find port for SMTP server?

Check your email provider’s help documentation for “SMTP settings.” It will list the server name, port and encryption type. If you use a hosting company’s mailbox, the settings are usually in your control panel under email accounts. When in doubt, try 587 with STARTTLS first.

Is SMTP always port 25?

No. Port 25 is the default SMTP port for server-to-server relay. Mail clients and apps should send on port 587 with STARTTLS or port 465 with implicit TLS. Port 2525 is an unofficial alternative some services offer.

What are the port numbers used for IMAP and POP3?

IMAP uses port 143 (plain or STARTTLS) and port 993 (implicit TLS). POP3 uses port 110 (plain or STARTTLS) and port 995 (implicit TLS). Use the encrypted ports, 993 and 995, whenever possible.

What is the difference between IMAP and POP3?

IMAP keeps your mail on the server and syncs it across every device, so reading or deleting on your phone shows up on your laptop. POP3 downloads messages to one device and, by default, removes them from the server. IMAP is the better choice for almost everyone today.

Which is more secure, port 465 or 587?

Both are secure when configured correctly. Port 465 encrypts from the first byte, which RFC 8314 prefers. Port 587 upgrades to encryption with STARTTLS before any login details are sent. Use whichever your provider supports.

A webhook is an automated HTTP message that one application sends to another the moment something happens, such as an email bouncing or a subscriber clicking unsubscribe. Your system doesn’t keep asking for updates. The sending service pushes the data to a URL you provide. Email platforms rely on webhooks to report deliveries, bounces, complaints, opens and clicks to your CRM, store or database in near real time.

What are webhooks, in plain terms?

Webhooks are user-defined HTTP callbacks. You register a URL with a service, choose the events you care about, and the service sends an HTTP request to that URL each time one of those events occurs. The request body carries the details: which event, when it happened, which message or contact it relates to.

The term dates to 2007, when developer Jeff Lindsay described “web hooks” as a way for web apps to notify each other the way Unix programs pass output through pipes. The idea caught on because it solved a common integration problem with very little machinery: any system that can receive an HTTP request can receive a webhook.

A useful analogy is the difference between refreshing a parcel tracking page every ten minutes and getting a text when the courier drops off the box. Polling an API is the refreshing. A webhook is the text.

People sometimes call webhooks “reverse APIs” or “push APIs”. The labels are loose, but they capture the key point. With a normal API call, you start the conversation. With a webhook, the other system does.

How a webhook works, step by step

Every webhook follows the same basic flow, regardless of which apps are involved:

1. You register an endpoint. This is a URL on your server or in an automation tool, for example https://example.com/hooks/email-events.
2. You pick the events. Most providers let you subscribe only to the events you need, such as bounces and spam complaints.
3. An event happens. A receiving mail server rejects a message, or a subscriber clicks a link.
4. The provider sends an HTTP POST. The request contains a payload, usually JSON, describing the event.
5. Your endpoint responds with a 2xx status code. This tells the provider the delivery worked. Anything else, or a timeout, usually triggers a retry.
6. Your code acts on the data. It might suppress an address, update a contact record or post an alert to Slack.

A semi-realistic webhook example

Say a subscriber’s mailbox no longer exists and the receiving server returns a hard bounce. SendGrid’s Event Webhook would send your endpoint a JSON array of events. A simplified version looks like this:

[
  {
    "email": "[email protected]",
    "timestamp": 1735689600,
    "event": "bounce",
    "type": "bounce",
    "reason": "550 5.1.1 The email account that you tried to reach does not exist",
    "status": "5.1.1",
    "sg_event_id": "a1b2c3d4e5f6",
    "sg_message_id": "14c5d75ce93.dfd.64b469.filter0001.16648.5515E0B88.0"
  }
]

Your code reads event, sees a hard bounce with a 5.1.1 status, marks [email protected] as undeliverable in your CRM and returns 200 OK. Total elapsed time from bounce to suppression: usually seconds.

Mailgun structures things differently. It wraps the event inside an event-data object and adds a separate signature object for verification:

{
  "signature": {
    "timestamp": "1735689600",
    "token": "a8ce0edb2dd8301dee6c2405235584e45aa91d1e9f979f3de0",
    "signature": "d2271d12299f6592d9d44cd9d250f0704e4674c30d79d07c47a66f95ce71cf55"
  },
  "event-data": {
    "event": "failed",
    "severity": "permanent",
    "recipient": "[email protected]",
    "id": "CPgfbmQMTCKtHW6uIWtuVe"
  }
}

Same event, different shape. That is the first lesson of working with email webhooks: every provider has its own payload format, so your handler needs to be written for the specific service sending to it.

Webhooks vs. APIs (and polling)

Webhooks and APIs aren’t competitors. Webhooks travel over HTTP and are part of a provider’s API surface. The real comparison is between push (webhooks) and pull (polling an API endpoint on a schedule).

	Webhook (push)	API polling (pull)
Who starts the request	The provider	Your application
Timing	Near real time, seconds after the event	Delayed by your polling interval
Wasted requests	None; a request means something happened	Many; most polls return nothing new
Rate limit pressure	Low	High at short intervals
What you need to run	A public HTTPS endpoint	A scheduled job and API credentials
Missed data risk	Events can be lost if your endpoint is down too long	Low; you can re-query history
Best for	Reacting to events as they happen	Backfills, reconciliation, bulk reads

The strongest setups use both. Webhooks handle the live flow, and a nightly API query catches anything that slipped through during an outage. Email providers make this easy because most of them expose an events or logs API alongside their webhooks.

How email services use webhooks

Sending an email kicks off a chain of events you can’t see from your own app. The provider accepts the message, hands it to the recipient’s mail server, and then gets back a delivery, a deferral or a bounce. Later, the recipient might open it, click it, mark it as spam or unsubscribe. Webhooks are how the provider tells you about each of those steps.

Here are the event types you’ll see across most email platforms and what you should do with each one.

Event	What it means	What your system should do
Delivered	Receiving server accepted the message	Log it; delivered does not mean inbox
Deferred / delayed	Temporary failure, provider will retry	Usually nothing; watch for spikes by domain
Hard bounce	Permanent failure, e.g. address doesn’t exist	Suppress the address immediately
Soft bounce	Temporary issue, e.g. full mailbox	Count them; suppress after repeated failures
Spam complaint	Recipient clicked “Report spam”	Unsubscribe them at once and flag the source
Unsubscribe	Recipient opted out	Update every system that can email them
Open	Tracking pixel loaded	Treat as a soft signal only (see below)
Click	Tracked link followed	Trigger follow-ups, score engagement
Dropped / rejected	Provider refused to send, often a suppressed address	Check why; fix the list or template

Why bounce and complaint webhooks matter most

If you only wire up two events, make them bounces and spam complaints. Gmail and Yahoo’s bulk sender requirements, enforced from February 2024 for anyone sending 5,000 or more messages a day to Gmail addresses, ask senders to keep their spam complaint rate below 0.3%. Google recommends staying under 0.1%. Microsoft added its own requirements for high-volume senders to Outlook.com addresses in May 2025.

Your email service already suppresses bounced and complaining addresses on its own sending infrastructure. The problem is the other systems. If your CRM, your e-commerce platform or a second email tool doesn’t know about the complaint, it may keep mailing that person. A complaint webhook closes that gap.

Unsubscribe webhooks are compliance plumbing

The same Gmail and Yahoo rules require one-click unsubscribe for marketing mail and expect opt-outs to be honoured within two days. In the US, CAN-SPAM gives you 10 business days. Under GDPR, a withdrawn consent has to stop processing for that purpose.

Those deadlines get tricky when you send from more than one tool. Your newsletter might go out through Mailchimp while receipts and win-back flows come from a transactional service. An unsubscribe webhook from one platform, pushed into your central contact record, is the simplest way to keep every system in sync.

Open events need a pinch of salt

Since Apple launched Mail Privacy Protection with iOS 15 in September 2021, Apple Mail can preload images (including tracking pixels) through proxy servers whether or not the person reads the email. That means a large share of “open” webhooks now fire automatically. Don’t build important automations on opens alone. Clicks, replies and purchases are far more trustworthy triggers.

Webhook support across major email providers

Every major email service offers webhooks, but the details differ in ways that affect your code. This table summarises how the main providers handle them, based on their published documentation at the time of writing (early 2025). Check the current docs before you build, as these change.

Provider	Webhook name	Payload format	Request signing	Retry behaviour
Twilio SendGrid	Event Webhook	JSON array, batched	Optional ECDSA signature (Signed Event Webhook)	Retries non-2xx responses for up to 24 hours
Mailgun	Webhooks (per domain)	JSON, one event per request	HMAC-SHA256 with your webhook signing key	Retries for about 8 hours; a 406 response stops retries
Postmark	Webhooks (per message stream)	JSON, one event per request	No signatures; supports Basic Auth and IP allowlisting	Retries failed deliveries with increasing delays
Amazon SES	Event publishing via SNS or EventBridge	JSON in an SNS or EventBridge envelope	SNS messages are signed by AWS	Governed by SNS or EventBridge delivery policy
Mailchimp (Marketing)	Audience webhooks	Form-encoded POST	No signatures; use a secret in the URL	Disables webhooks that keep failing
Mailchimp Transactional (Mandrill)	Webhooks	Form-encoded batch of JSON events	HMAC-SHA1 via X-Mandrill-Signature	Retries failed batches
Resend	Webhooks	JSON, one event per request	Signed via Svix headers	Retries on a backoff schedule

A few practical takeaways from that table:

• SendGrid batches. One request may contain dozens of events, so your handler must loop through the array.
• Mailgun lets you say “stop”. Returning 406 Not Acceptable tells it not to retry that event.
• Postmark and Mailchimp don’t sign requests. You need Basic Auth, an IP allowlist or a hard-to-guess token in the URL to keep strangers from posting fake events.
• Amazon SES isn’t a classic webhook. You publish events through a configuration set to SNS (which can call an HTTPS endpoint) or EventBridge. You also have to confirm the SNS subscription before events flow.

Most common use cases for webhooks in email

Beyond bounce and complaint handling, here is where webhooks earn their keep for email teams:

• CRM sync. Push clicks, unsubscribes and bounces into HubSpot, Salesforce or your own database so sales and support see the same contact status as marketing.
• E-commerce triggers. Shopify, WooCommerce and Stripe all send webhooks for orders, refunds and failed payments. Your email platform (or a middleware tool) catches them and fires order confirmations, shipping updates and dunning emails. These receipts get used in more places than you might expect, since Google says Chrome autofill can now pull order and flight details from Gmail.
• Double opt-in. A signup form posts to your email platform, and a subscribe webhook tells your app to unlock a download or create an account.
• Team alerts. Send a Slack or Teams message when complaint events spike, or when a key customer’s emails start bouncing.
• Data warehouse loading. Stream every event into BigQuery, Snowflake or Postgres for long-term reporting that outlives your provider’s log retention.
• Inbound email. Most transactional providers can parse replies sent to your domain and post them to a webhook, which is how many support desks and reply-to-comment features work.

No-code tools like Zapier, Make and n8n give you a webhook URL in a few clicks. That’s the quickest way to try these use cases before you write any code.

How to set up an email webhook

Menu paths below were accurate at the time of writing. Providers redesign their dashboards often, so look for “Webhooks” or “Event Webhook” under settings if a label has moved.

• SendGrid: Settings > Mail Settings > Event Webhooks
• Mailgun: Send > Sending > Webhooks, then choose the domain
• Postmark: Servers > your server > your message stream > Webhooks
• Amazon SES: Configuration sets > your set > Event destinations
• Mailchimp: Audience > Manage Audience > Settings > Webhooks

Before you write real code, point the webhook at a request inspection service or a local tunnel such as ngrok to see the exact payload. It saves guesswork about field names.

Securing your webhook endpoint

A webhook URL is a public door into your system. Anyone who finds it can post fake “unsubscribe” or “bounce” events and quietly wreck your list. Lock it down with these layers:

1. Use HTTPS only. Never accept webhook data over plain HTTP.
2. Verify signatures. Where the provider signs requests, recompute the signature with your secret key and compare it before trusting anything in the body.
3. Check timestamps. Reject requests older than a few minutes to block replay attacks.
4. Add Basic Auth or a URL token for providers that don’t sign requests.
5. Allowlist IPs where the provider publishes its sending ranges.

Here is how Mailgun signature verification looks in Python. Mailgun concatenates the timestamp and token, then signs them with HMAC-SHA256 using your webhook signing key:

import hashlib
import hmac def verify_mailgun(signing_key, timestamp, token, signature):
    expected = hmac.new(
        key=signing_key.encode(),
        msg=f"{timestamp}{token}".encode(),
        digestmod=hashlib.sha256,
    ).hexdigest()
    return hmac.compare_digest(expected, signature)

Use compare_digest rather than == so the comparison takes constant time. For extra protection, store each token you’ve seen and reject repeats.

A growing number of services, including those built on Svix, follow the Standard Webhooks specification. It uses three headers (webhook-id, webhook-timestamp and webhook-signature), which means one verification routine can cover several providers.

Webhook challenges: how to troubleshoot common issues

Most webhook problems fall into a handful of patterns. Start here when events go missing or arrive twice.

Symptom	Likely cause	Fix
No events arriving at all	Wrong URL, firewall block, or SES SNS subscription not confirmed	Send a test event; check server logs; confirm the SNS subscription
Provider shows repeated failures	Endpoint returns non-2xx or times out	Return 200 immediately, then process in the background
Same event processed twice	Retries after a slow response; at-least-once delivery	Deduplicate on the event ID (e.g. SendGrid’s sg_event_id)
Events in the “wrong” order	Parallel delivery and retries	Sort by the event timestamp, not arrival time
Signature check always fails	Body parsed or re-encoded before verification, or wrong key	Verify against the raw request body; confirm the key
Mailchimp webhook won’t save	Mailchimp validates the URL with a GET request first	Make the endpoint return 200 to GET as well as POST
Huge spike after an outage	Provider replaying its retry queue	Queue incoming events; scale workers, not the endpoint
Webhook silently disabled	Too many consecutive failures	Re-enable it, then backfill from the provider’s events API

The second row causes more trouble than all the others combined. Providers expect a fast answer, and some time out after just a few seconds. If your handler calls three other APIs before responding, you’ll see timeouts, retries and duplicates.

Tips for optimizing webhook usage

These habits separate a webhook integration that runs quietly for years from one that pages you at 3 a.m.

Acknowledge first, work later. Write the raw payload to a queue or table and return 200 straight away. A separate worker handles the business logic. This keeps you inside every provider’s timeout and lets you replay events if your code has a bug.

Make handlers idempotent. Assume every event will arrive at least twice at some point. Processing a bounce twice should give the same result as processing it once.

Subscribe to less. If you don’t use open events, turn them off. A large newsletter send can generate an open webhook for most Apple Mail recipients within minutes, and that’s a lot of traffic to receive and discard.

Keep the raw payloads. Providers retain event logs for a limited period, often days or weeks depending on plan. Your own copy lets you answer “why did this person stop getting emails?” months later.

Monitor the endpoint. Alert on rising error rates, falling event volume and queue backlog. A webhook that quietly stops is worse than one that fails loudly.

Reconcile on a schedule. Run a daily job that pulls suppressions or events through the provider’s API and compares them with your records. It catches anything lost during downtime.

Separate environments. Use different endpoints and signing keys for staging and production so test sends never touch real contact records.

Benefits of using webhooks

For an email program, the payoff is concrete:

• Faster list hygiene. Bad addresses are suppressed everywhere in seconds, not on the next nightly sync.
• Lower complaint rates. Complainers stop receiving mail from every tool, protecting your sender reputation.
• Fewer API calls. No polling loops eating into rate limits.
• Better automation triggers. Clicks and purchases can start follow-up sequences while the subscriber is still engaged.
• Simpler architecture. Any system that can accept an HTTP POST can join the integration.

The cost is that you now run an endpoint that must be available, secure and fast. For most teams that trade is well worth it, especially once the sending volume puts you under Gmail, Yahoo and Microsoft’s bulk sender rules.

FAQ

What is a webhook in simple terms?

A webhook is a message one app sends to another automatically when something happens. Instead of your system repeatedly asking “anything new?”, the other service sends an HTTP request to a URL you gave it, with details of the event.

What are webhooks used for in email marketing?

Mainly for syncing email events to other systems: suppressing hard bounces, unsubscribing people who report spam, updating CRM records with clicks, triggering follow-up emails and loading event data into reporting tools.

Is a webhook the same as an API?

No. An API is something you call when you want data. A webhook is a call the provider makes to you when an event occurs. Both use HTTP, and most email services offer both, so you can react in real time with webhooks and fill gaps with API queries.

Do webhooks always deliver every event?

No delivery system is perfect. Most providers retry failed deliveries for a set window (24 hours for SendGrid, roughly 8 to 12 hours for Mailgun depending on which of its docs you consult), but if your endpoint is down longer than that, events can be lost. A daily reconciliation job through the provider’s API covers the gap.

Do I need to be a developer to use webhooks?

Not to get started. Zapier, Make and n8n generate webhook URLs you can paste into your email platform and connect to Slack, Google Sheets or a CRM without code. For high volumes or compliance-critical events like unsubscribes, a coded endpoint with signature checks is the safer choice.

Are webhooks secure?

They are as secure as your endpoint. Use HTTPS, verify signatures where the provider offers them, reject old timestamps and add Basic Auth or IP allowlisting for providers that don’t sign requests.