Sending Cold Email To Outlook

It’s no secret that cold email delivery is getting tougher and tougher. And that’s expecially true if you’re sending cold email to Outlook.

So in this article I’ll show you what’s working in the world of Outlook delivery for cold email. These are insights that I’ve gained after conducting a lot of tests and speaking to other trusted sources who’ve conducted extensive tests as well. This article is meant to be a snapshot in time (November 2024) – best practices will change again in the near future.

I’m not just guessing about Outlook delivery. We’ve been conducting widespread tests for the past 2-3 weeks and are also a part of a few private groups where we’re testing every single day to see what’s working and what’s not. The tips and insights I’m about to share come straight from spending thousands of dollars and getting real world results. I’ve also included insights from deliverability pros like Jesse Oulette for a comprehensive overview.

Now, to give you some context, before we started testing our client results mostly looked like this: 

As you can see, we sent 3290 emails and only got 2 replies. Something was broken and it was pretty obvious we weren’t getting responses because we weren’t getting inboxed.

Fortunately this story has a happy ending. Once we figured out what works for us, our results went from the non-results above to:

It’s a MASSIVE improvement! And here’s what we did to achieve it.

Recent Deliverability For Outlook

First, we needed to better understand the current cold email environment. Deliverability has been changing fast lately – here’s what’s going on:

• Email providers are getting stricter: They’re using AI to spot cold emails and send them to spam. 
• ESP Matching: Around 2 weeks back, ESP matching was a bad idea but it’s working now. Google → Google, Google → Custom ESPs, Carrier Pigeon → Outlook.
• Enterprise-level security is tough: Extra layers of security like Mimecast and Proofpoint make reaching enterprise inboxes harder. If you are reaching out to them, make sure your offer is good and you don’t give them a good enough reason to mark you as spam.
• The landscape is constantly shifting: Just 2-3 weeks ago, Gmail inboxes were nearly impossible to reach. Now, Outlook is acting up.

For example, even when sending from Gmail to Gmail (which is usually best), 30% of emails still end up in spam.

What’s The Impact? 

These changes have made cold emailing harder:

• Lower inbox rates: A lot of cold emails are going straight to spam, even with the right setup.
• Outlook is extremely difficult: A whopping 83% of emails sent to Outlook are landing in spam.
• Gmail is somewhat better: But still, 42% of emails from Outlook to Gmail go to spam.
• Constant adaptation is necessary: What worked last week might not work today.

Our Current Deliverability Stack

Inboxes:

• Google
• Outlook
• SMTP – Mailreef and Maildoso

Sequencer:

• Smartlead
• Instantly
• Private Sequencer

Deliverability Tools:

• EmailGuard
• SmartDelivery

Warmup vs No Warmup:

Interestingly, we’re landing in the inbox (for now) without warmup. The important thing to note here is we sent very low volume per inbox. These days you can’t be sending 25-30 / inbox anymore. We’re sending 2-10 / inbox / day with slow or no ramp-up.

For outlook inbox delivery we aren’t ramping up with warm up and are sticking to very low volume.

Private IP vs Public IP

A big topic of conversation these days is public vs private IP addresses for cold email. For each of our clients, we are using private IPs and servers for sending.

Using public warmup pools and public IPs might not be the best way forward since ESPs are figuring out everything slowly. It’s a good idea to diversify here as well.

If you are looking for a more details about this I recommend you check out Taylor Harren’s post on LinkedIn.

How to land in the Outlook inbox

While there’s no 100% guarantee, here are some tips to improve your chances of getting good delivery to Outlook:

Start by analyzing your ICP and to see what inboxes they use. Some industries are more likely to use Google or Outlook than others. Based on your findings, build your tech stack.

Match your email provider to your what’s working at the time: If Google to Google isn’t working, then use Outlook or SMTP to send to Google. If Google to Outlook isn’t working, use Outlook or SMTP to send to Outlook and so on. Adapt to what’s working so your results don’t tank.

Use tooks like EmailGuard or Leadmagic to group your contacts by their email provider (Google, Microsoft, Custom ESPs and ENT ESPs). Then segment your email list for sending.

Spintax is becoming less effective as ESPs are figuring out ways to spot it in real time. Instead, use Clay to generate variable phrases / sentences for each lead. If you’re sending a lot of volume then change your copy every 2 weeks or so.

Diversify your ESPs: We’re currently using a mix of Google, Enterprise Outlook, and 2 SMTP providers.

Domain masking can potentially improve reply rates by 1-2% when sending to custom and enterprise ESPs.

Do weekly inboxing tests to monitor delivery. These tests aren’t perfect but they’ll help you identify what’s working, and where you can improve.

How to land in Outlook right now

Outlook is ‘impossible’ to inbox into but we still manage. ScaledMail and Maildoso are landing in Outlook inboxes from day one, even without warmup.

 

• The image above is an inbox placement test conducted in Oct 2024 using ScaledMail.
• We also have a few clients who target enterprise companies. ScaledMail is working well for this.
• Maildoso might not be the best if you are reaching out to enterprise. Use it if you are targeting mid-market SMBs.

Outlook is still challenging and we don’t when this will change. But tools like ScaledMail and Maildoso are showing promising results.

Final Notes:

Here are some final notes on Outlook delivery for cold email.

1. Offer is king. We have one client who is using 2-3 year old google inboxes and still landing in Outlook inboxes even now.
2. Diversify ESPs.
3. Test, test and test.
4. No warmup is working better at the moment but not sure about the life of domains.
5. Masking yields better results when reaching out to ENT ESPs. 
6. Using same copy for an extended time will lead to getting fingerprinted.
7. Google, Outlook and Mailreef aren’t landing in Outlook (as of 20/10/24) whereas ScaledMail and Maildoso are. Hypertide as well from what I’ve heard.
8. Deliverability will be getting harder as AI becomes better and better. Cold email isn’t going anywhere but if you don’t adapt, then you gotta go.

Thanks for reading until here. If you have any interesting findings that you’d like to share, feel free to hit me up on LinkedIn!

Happy Sending 🚀

This resource was crafted to help give you an overview on what’s going on with deliverability and how you can increase your chances of landing in the inbox.

If you found this helpful and are seeking more personalised guidance, I am happy to  connect on LinkedIn.