Is anyone else having trouble sending email to @hotmail and @outlook clients?

We have an invite system. It goes through Sendgrid, and it sends out a personalized email. So far no issues sending email to every domain name and email cliente except hotmail and outlook (I know, who uses hotmail these days!).

Is anyone else having issues with these?

Sendgrid is reporting that hotmail is blocking the emails:

What’s weird is, zero issue with gmail, yahoo and other email services. It’s just outlook’s servers that seem to block us.

From my limited experience, Hotmail and Outlook love blacklisting IPs. If you are on Basic/Essentials plan on Sendgrid, your emails get sent from the same IP as potentially hundreds of other sites… If one of those sends bad emails and gets blacklisted, it affects everyone at once on that IP.

If I were in your shoes, I’d evaluate getting a dedicated IP with Sendgrid - Which unfortunately requires a Pro plan…

I’m sure others will have other possible explanations. Just my 2 cents.

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This is very interesting, and it makes sense. I’m on the essentials plan, so moving to a pro plan is a 3x price jump, but might be worth testing. I’ve contacted Sendgrid, let’s see what they come up with.

Hey Bud, check out this post on the same topic. I’m not ok with Sendgrid’s approach on this and will be migrating away. Currently thinking of

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Was having the same issue with a client’s app last week. Make sure you do everything you can to optimize for deliverability on Sendgrid’s end (domain validation, link branding, and reverse DNS). You can find this in Sendgrid under “Sender Authentication”.

We ended up upgrading to the pro plan and emails are coming through perfectly now.

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Oh wow, does seem to be an issue! It’s just as painful as the quoted poster has stated. Email is pretty essential.

Thanks for the tip, will also check out. I’m waiting on Sendgrid’s reply and will post once I get an answer from them, hopefully we can get to the bottom of this!

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Some of Sendgrids IP addresses for sending are blacklisted by those email providers. The unfortunate part is Sendgrid won’t move your account to a server with a good reputation unless you upgrade an account.

Personally I made the switch to Postmark and am loving it. They focus on deliverability and speed and have a dedicated bootstrapped team that provide great customer service.


That’s one hell of a review! WIll check em out, thanks for the tip!

I switched to Postmark too. Did you follow any guide to set it up?

Nope, just their API documentation which is fairly good. If you are new to APIs it could be a little time consuming to get right though

Yup, on a paid SendGrid plan (lowest tier) but most mails do not reach yahoo, live, hotmail, or outlook (outright blocked or land in spam). Our emails are purely transactional. I’m looking into PostMark now.

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You can use the free Rich PostMark plugin. It’s very simple to use, created by @vini_brito