Survive Microsoft's Email Crackdown

Jeremy and Jack explore Microsoft's new email deliverability challenges for cold emails and share strategies to overcome them.

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What is the importance of dynamic content in emails?

Dynamic content enhances both deliverability and engagement.

"I take it for granted that most cold emailers have some level of dynamic content... even if it's just a name and a company."

Takeaway:
  • Dynamic content personalizes emails, reducing spam flags.
  • Incorporate merge fields or dynamic variables in your campaigns.
  • Personalization boosts recipient engagement and response rates.

How to avoid static messages in email campaigns?

Static messages can lead to deliverability issues.

"It really is about a static message. And how many times that static message is sent? For Microsoft?"

Takeaway:
  • Sending the same message repeatedly can trigger spam filters.
  • Personalize or reword messages to keep content fresh.
  • Use dynamic content to improve engagement and deliverability.

Why is monitoring bounces crucial?

Keeping an eye on bounces helps maintain email health.

"We also introduced... when there is a sender bounce... we pause it automatically... rather than actually keeping on trying to send and... you end up with like 500 bounces."

Takeaway:
  • Automated pause on bounces prevents further deliverability damage.
  • Regularly monitor and address bounces promptly.
  • Implement systems to manage bounces efficiently.

How to diversify your email sending platforms?

Using multiple platforms can minimize deliverability risks.

"You should diversify your sending... when it happened to us, we switched to Google Workspace and that was very good."

Takeaway:
  • Relying on one platform can be risky if deliverability issues arise.
  • Diversify by using platforms like Gmail and Microsoft.
  • Having alternatives ensures continued campaign performance.

What are the risks of using auto warm-up tools excessively?

Misusing auto warm-up tools can lead to email blocking.

"People... register to a lot of auto warm up or they have the same auto warm up and they crank it up... you're going to trigger some alerts and then you risk your account being blocked."

Takeaway:
  • Overusing auto warm-up tools can cause deliverability issues.
  • Keep warm-up activities within reasonable limits.
  • Understand the impact of warm-up tools on your sending volume.

Why should you avoid aggressive follow-up sequences?

Overloading recipients with follow-ups can harm deliverability.

"If you have like a very aggressive follow up sequences towards your volume... that's very important."

Takeaway:
  • Excessive follow-ups can trigger spam filters.
  • Balance your follow-up frequency to avoid being flagged.
  • Monitor engagement to adjust follow-up strategies.

How can AI help improve email deliverability?

Leveraging AI can enhance email uniqueness and deliverability.

"I just woke up and I started actually just designing the thing and programming the thing and 12 hours later... we call it Reword... we reword with AI every email we're sending."

Takeaway:
  • AI can rephrase emails to create unique messages automatically.
  • Unique emails are less likely to be flagged by spam filters.
  • Implement AI tools to reword emails for better deliverability.

How does identical content trigger spam filters?

Sending identical emails can lead to delivery problems with Microsoft.

"We realized that if we give the feedback to enable reword on your output, so they won't actually look the same... then actually just leads to people being able to have their campaign uninterrupted."

Takeaway:
  • Microsoft detects and blocks emails with identical content.
  • Rewording emails makes each message unique, reducing spam flags.
  • Utilize tools or AI to vary your email content.

Why does Microsoft block emails due to volume spikes?

Understanding why Microsoft blocks emails can help marketers avoid deliverability issues.

"If you think about it again, from the point of view of Microsoft... they imagine people to just either get infected by a virus and then start blasting... always the same sort of messages."

Takeaway:
  • Sudden spikes in email volume can trigger Microsoft's spam filters.
  • Gradually ramp up your sending volume to avoid being flagged.
  • Monitor your sending patterns to maintain consistent volumes.

How to prevent Microsoft email bounces?

Email marketers are facing challenges with deliverability, especially when sending via Microsoft accounts.

"Bounces—bounces from Microsoft basically, it's what we call sender bounces. So someone tried to send and Microsoft said no, I'm not going to send your email. It looks like spam."

Takeaway:
  • Microsoft's stricter spam filters may cause legitimate emails to bounce.
  • Marketers should be aware of these changes to adjust their strategies accordingly.
  • Contacting Microsoft support can help resolve deliverability issues.

Episode Info:

Title:
#381 - Microsoft's Email Crackdown: Secrets to Keep Your Cold Emails Going
Episode Link:
Keywords:
Microsoft email deliverability, cold email strategies, email best practices
Episode Air Date:
November 6, 2024

Podcast info:

Show Name:
Cold Email Outreach
Author:
Jeremy Chatelaine and Jack Reamer
Owner:
Jeremy Chatelaine
Category:
Business - Marketing

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