Issue #191 All About Email

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Hi, friend. 👋

Welcome to Issue #191 of All About Email!

Last week, we completed our two-part mini-series look at engagement, and there is a special highlight on accessibility.

This week, we take a closer look at whether Gmail was spamming emails with Vimeo links and what it teaches us about links in emails.

Let’s go! 👇

Is Gmail Spamming Emails With Vimeo Links?

Last week, I saw a post on X from Alyssa Dulin (Sr. Manager of Creator Growth and Deliverability at Kit), which I reposted on LinkedIn.

🚨 It got picked up in the “Email Geeks” Slack, and I explored the rabbit hole, which revealed some important information about links and how they can impact deliverability.

So What Happened?

For anyone who doesn’t know Alyssa, she knows her stuff around deliverability and co-hosted the Deliverability Defined podcast.

Here’s the context from Alyssa:

💡 Alyssa shared that as soon as the Vimeo link is removed (from the email), the warning goes away and the email lands in the inbox again.

Below is the image that is shown in Gmail.

Was it just a Platform Issue?

🤔 It is possible friend, (and was suggested in the Email Geeks Slack) that this might have been a platform-specific issue (in this case, Kit).

However, others in different Reddit channels noticed similar issues:

• With Vimeo links in email signatures.

• The issue seems to have started around April 21st, 2025.

I’ve not been able to test the issue myself yet, but other platforms were able to test and not replicate what was happening for some Kit users (from the information we have, not all Kit customers had this issue).

Was it the Type of Vimeo link?

I don’t know whether the impacted Kit users were using public or private Vimeo links, but there has been a suggestion that private videos “might” be more likely to trigger spam.

The reasoning is that some suspected that URLs with extra tokens (for unlisted videos) looked more “sketchy” to filters (it’s possible, but again, we don’t quite know).

The Expert Opinion

So with the Vimeo domain not being blacklisted and no apparent pattern to public or private Vimeo links was it:

• A Gmail bug?

• A pattern of poor behaviour and engagement for these specific senders?

• Something else?

🤔 Steve Atkins from Word to the Wise notes that the emails weren’t just going to spam, they were getting a “pretty specific warning”.

🕵️‍♂️ Steve and Al Iverson (Valimail) wondered if the tracking URLs in Kit were causing the issue, but Alyssa ruled this out.

🧠 Chris Byrne (Sensorpro) suggested a “common gotcha” with Vimeo is forgetting to set a rating, which will force a Vimeo login, which “might” be a factor.

Further investigations from Chris suggested Vimeo may have site issues that Gmail is picking up on.

⚡️ Jesse Hanley (Bento) had experienced a similar issue with YouTube shortened URLs and concluded it was a combination of links (our domain x the YouTube shortened URL). No action was taken, and it returned to normal in 24 hours.

Jesse suggested: “There is a chance someone is doing forwarding spam with a Kit template, and Gmail’s machine learning is incorrectly flagging the combo of domains as bad.”

A Vimeo Issue or Links in General?

🚨 It’s important to note, friend, that this is not just a Kit or Vimeo issue.

It’s a link issue, and other ESPs have been impacted in the past and will be impacted in the future:

• Al Iverson noted past problems with the Bit.ly URL Shortener.

• Alyssa also noted (like other ESPs) that she has seen issues with shortened YouTube URLs causing similar trigger warnings in Gmail.

💡 Even if our domain/sender reputation is good, linking to external domains can be a calculated risk, as we don’t control those domains.

Best Practices for Links

I’ve looked at email best practices in detail, so the list below isn’t exhaustive, and the final point is perhaps the most important.

1. Use Custom Domains for Tracking: Ensure your email service (I use Beehiiv, which offers this) is configured with your tracking domain (e.g., links.yourdomain.com) rather than a generic ESP domain. This keeps the link pathway branded and under your control. **
   

2. Avoid URL Shorteners or Strange Redirects - They can hide the final URL. The more transparent and direct your link, the better. Gmail is more likely to trust links that don’t have convoluted forwarding.
   

3. Test, Test, Test: Before sending a big campaign, send test emails to a few Gmail accounts. If the email with the video link lands in spam, you just saved yourself a world of pain. Adjust the approach (e.g. remove or change the link) and test again.
   

4. Keep Overall Email Quality High: Don’t give spam filters any extra reasons to doubt you. Authenticate your emails, follow best practices and keep your list engaged and clean. These all contribute to a positive reputation, which can sometimes override a borderline element in your content.

** (Similarly, some video services allow a custom CNAME for sharing links – use it if available, so that the link appears to be from your domain.)

Have You Had Issues With Vimeo Links?

🧠 If you’ve had issues with Vimeo links in your emails, friend (either sending or receiving), I would love to hear from you.

Reply to this email and let me know if it’s “all good” or if you’ve had a bumpy ride recently with Vimeo links.

💡At the time of publishing, I don’t know if the Vimeo issue is resolved for those handful of customers at Kit (I have reached out for more information).

I’ll leave you with this parting thought and wise words from Alyssa:

All About Email - Playlist 🎧

I listen to a lot of music, friend, especially when writing newsletters.

When I hit the publish button each week, I’ll share the track I’m listening to and build the craziest playlist you’ve probably ever heard.

Sponsorship Opportunities

🚨 If you’re interested in sponsoring the “All About Email” newsletter, you can find all the details in this Google Doc. I currently have “Classified” slots and a Main Sponsor slot available.

That’s It For This Week 👋

🚨 It’s coming close to the 200th issue of my newsletter, over four years of writing (if you include holidays), and I want to celebrate with something special.

⚠️ Last call if anyone wants to provide a special offer for my readers, reply to this email and let me know how you can help.

See you next week!

Email Marketing News & Tips

This week's excellent and insightful email news & tips:

• Email Deliverability Tests - Why We No Longer Publish Bi-Annual Tests (And What We Do Instead). (Email Tooltester)

• List Building - How I Used a Lead Magnet to Grow My Email List By 22%. (Inbox Collective)

• Improving Email Validation - With AI and Large Language Models (LLMs). (ZeroBounce)

• Screaming Into the Void - Why Can Proving Email's Value Internally Feel Like This? (Lauren Meyer)

• Automation - Combating automated interactions in email marketing analytics. (Customer.io)

• Reach Metrics - SEINō releases a demo of their new “Reach Metrics” to give better insight into real reach, mail pressure, and engagement over time. (SEINō)

• Regional deep dives - Find the unique attitudes, habits, and spending propensities in 9 different markets. (Mailchimp)

• Impactful Personalisation - That doesn’t mean just slapping “Dear FirstName” at the top and calling it a day. (Alison Gootee)

• Free Webinar - What is the European Accessibility Act (EAA) and what does it mean for email developers and email senders? (Sinch)

• Semantics - Structural Content in Email Accessibility. (Sarah Gallardo)

• Quality over Quantity - We have it backwards and obsess over how to wake the “unengaged”. (cr. Carin Slater). (Jay Schwedelson)

• Gold Magnet? - How Olly Richards Turned a Free Google Doc into $1.2M and 18K Newsletter Subscribers. (Growth in Reverse)

• Prediction - Every serious email player will use multiple ESPs in the next 12 months. (Matt McGarry)

• Welcome Email Subject Lines - How to Get That All-Important First Open. (Email Tooltester)

If you have a question about this email or email marketing, reply, and I will answer you as soon as possible.

I hope you have a great week! 👋