Comments on: Practical Exchange: Understanding SMTP Relay in Exchange Online https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/ Practical Office 365 News, Tips, and Tutorials Wed, 10 Jul 2024 16:23:20 +0000 hourly 1 https://wordpress.org/?v=6.6.1 By: Mike Donovan https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-296655 Wed, 10 Jul 2024 16:23:20 +0000 https://practical365.com/?p=61004#comment-296655 This article caught my eye because anyone who is trying to remove all on-premise servers will need to consider the very issues discussed in this article. I have a couple of general comments that I hope are relevant.
1) IIS6 has little to no PowerShell support. But there are visual basic scripts around for bulk adds, bulk removes and exporting the list of IP’s being relayed.
2) Microsoft, at one point, was pointing people to SendGrid (which turns out to be a rather good solution.) The authentication limitations however may limit its use in some situations. What we ran into were a) no login flexibility; it always must be APIKey as the authentication login and b) the password length is 69 characters. Many older printers and other devices don’t support passwords longer than ~40 characters.
3) We tried using Smtp.office365.com initially (this was years ago.) It was not consistent and failed to authenticate intermittently. That may have been fixed. But it was not a stable alternative at the time we considered it.
I have been scouring the exchange blogs and other resources for quite some time for relay alternatives. This is the most comprehensive and detailed discussion I have seen yet. Bravo for addressing this!

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By: Chris https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-296479 Fri, 05 Jul 2024 21:07:34 +0000 https://practical365.com/?p=61004#comment-296479 Anyone use a 3rd party provider like SMTP2GO for this? I’m trialing it out now and to be honest for $10/mo it was pretty easy to setup.

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By: <div class="apbct-real-user-wrapper"> <div class="apbct-real-user-author-name">Tony Redmond</div> <div class="apbct-real-user-badge" onmouseover=" let popup = document.getElementById('apbct_trp_comment_id_295473'); popup.style.display = 'inline-flex'; "> <div class="apbct-real-user-popup" id="apbct_trp_comment_id_295473"> <div class="apbct-real-user-title"> <p class="apbct-real-user-popup-header">The Real Person!</p> <p class="apbct-real-user-popup-text">Author <b>Tony Redmond</b> acts as a real person and passed all tests against spambots. Anti-Spam by CleanTalk.</p> </div> </div> </div> </div> https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-295473 Fri, 14 Jun 2024 09:40:15 +0000 https://practical365.com/?p=61004#comment-295473 In reply to Cyril.

Unfortunately, Practical365.com cannot create a solution out of thin air. We also cannot report information that Microsoft has shared with our authors under NDA. I think it is fair to say that all of the folks here who work with Exchange Server and Exchange Online are intensely aware of the issue around SMTP relay. Microsoft is as well, but again, we cannot report what doesn’t exist today and what might not exist if development plans fail. If you want to read about aspirational delivery of software, read Microsoft’s blogs where they can describe future plans and dates. If you want to read what’s available and can be implemented today, read our articles.

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By: Cyril https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-295469 Fri, 14 Jun 2024 08:50:57 +0000 https://practical365.com/?p=61004#comment-295469 In reply to Jaap Wesselius.

I posted my comments to warn some community members, that would chose a path, maybe consume time to make a long-term configuration, with some options that will sadly be deprecated. Unless they are, they can be used obviously, but don’t spend to much time configuring a state-of-the-art relay system that won’t work in a few months.
The problem here is, many messaging admins are missing solutions from Microsoft. Microsoft deprecating old products or auth protocols is indeed a good news, but we need alternatives. Especially as some companies already got rid of their Exchange Servers. With Microsoft deprecating SMTP AUTH online, we still need to relay emails from old appliances, we need a non-Exchange Server working and above all supported SMTP relay solution, that’s the situation in the current world, whether Microsoft likes it or not. I think it’s therefore a sensitive subject for Messaging admins at this time, and when we see this kind of title in an article, we all hope to see the miraculous announcement or solution we are all waiting for, therefore creating some disappointment. But this situation is Microsoft’s fault, not yours, thanks for sharing your knowledge and solutions to the community, it’s as precious as the time you’re saving us with clear explanations.

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By: Jaap Wesselius https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-295427 Thu, 13 Jun 2024 19:36:30 +0000 https://practical365.com/?p=61004#comment-295427 Thanks everyone for all the comments.
Overall it’s a bad story here from Microsoft. Customer want to get away from their Exchange servers, but there’s not really a good alternative here. Yes, you can use the SMTP service in Windows 2019 and Windows 2022 (the MMC issue turned out to be an entry in the Metabase.xml file) but despite it is in Windows 2022, it was part of IIS6 and as such not supported. HVE is on the horizon, but only targeted for internal recipients and ACS is a paid service.
SMTP AUTH is still available in Exchange Online and widely used. Millions of applications and devices can only do this, so I don’t see this going away anytime soon (that’s my personal opinion). So yes, it’s a bad story.
And about my time… I’m not a professional writer, I’m a consultant and working full time with customers on all sorts of Exchange things and I write about things I see in real life (and which I can repro in my lab) in my spare time.
And if you think you can do better (no pun intended) feel free to contact us to become an author as well, you are more than welcome.
I will try to make some changes to the article regarding the things I just mentioned and the comments that are left here.
Thanks all.

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By: <div class="apbct-real-user-wrapper"> <div class="apbct-real-user-author-name">Tony Redmond</div> <div class="apbct-real-user-badge" onmouseover=" let popup = document.getElementById('apbct_trp_comment_id_295419'); popup.style.display = 'inline-flex'; "> <div class="apbct-real-user-popup" id="apbct_trp_comment_id_295419"> <div class="apbct-real-user-title"> <p class="apbct-real-user-popup-header">The Real Person!</p> <p class="apbct-real-user-popup-text">Author <b>Tony Redmond</b> acts as a real person and passed all tests against spambots. Anti-Spam by CleanTalk.</p> </div> </div> </div> </div> https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-295419 Thu, 13 Jun 2024 16:22:11 +0000 https://practical365.com/?p=61004#comment-295419 In reply to Tony Redmond.

By the way, it’s always easy to criticize writers. If you’re up to the challenge, try writing for Practical 365 and see how it goes…

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By: Tony Redmond https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-295418 Thu, 13 Jun 2024 16:20:57 +0000 https://practical365.com/?p=61004#comment-295418 In reply to Miriam.

AFAIK, Exchange Server 2019 is the current version and will not be replaced untl Exchange Server Subscription arrives Edition arrives in Summer 2025. I think it is perfectly acceptable to discuss Exchange 2019 at this point.

SMTP AUTH and Basic AUTH are still available in Exchange Server. SMTP AUTH will be removed from Exchange Online, but it’s still there.

ERR won’t be in Exchange Online until 2025. HVE is still in preview and it and ACS will incur additional cost. I would like to write about HVE but I cannot because Microsoft cannot resolve a problem in my tenant (expected in previews). I don’t write about stuff until I have tested it thoroughly and I suspect that’s the same for Jaap.

The audience for Practical 365 is formed largely of people who need practical, hands-on advice for running online or on-premises environments. As it happens, the author of this piece is a highly experienced Exchange MVP who has huge knowledge of solving customer problems. Whether or not he didn’t care to spend time figuring out why an MMC snap-in failed is immaterial if his advice is sound and accurate.

If you care to read the articles on this site, I think you’ll find that they cover real-life topics with a very practical perspective. I think we’re well ahead of any other site writing about Microsoft 365 and Exchange Server today. If you can point to other sites that have published hundreds of articles about different topics in these areas that does better, I am all ears because I have not found one. There are always one-off articles that document invaluable nuggets of information that cannot be found elsewhere, but the value of a site is measured over time and not by individual articles.

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By: Miriam https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-295404 Thu, 13 Jun 2024 11:37:10 +0000 https://practical365.com/?p=61004#comment-295404 I was excited to see an article about SMTP Relay in Exchange Online, but I’m disappointed to see only obsolete or soon-to-be-obsolete options (Server 2019, SMTP AUTH, Basic Auth, ERR) without pointing those out and relying on readers’ comments to bring up that these features are short-lived or have limitations?

Is the audience of this article subject matter experts that can read between the lines and already know what works and what doesn’t or is the audience less-experienced admins trying to learn about technologies to use in their environments? I would have thought the latter and for those, this article is misleading.

And what is it with “I was not able to get the MMC snap-in working and I didn’t have enough time to figure out what was wrong there.” If someone doesn’t have enough time to figure out a problem, should they just omit details from their post or should they spend the time figuring it out before they post? I think that’s a no brainer.

Lastly, why not mention HVE or Azure Communication Services in an article about Exchange Online and SMTP relay?

Is the quality of this post representative of other articles on this site?

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By: Jaap Wesselius https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-295348 Wed, 12 Jun 2024 07:35:03 +0000 https://practical365.com/?p=61004#comment-295348 I know where you’re coming from, but what you say is not true.
IIS is supported, but the SMTP stack is part of the old IIS6 bits and that’s not supported for a long time now. But the bits are still in Windows (how odd, I think nobody cares to remove it from the source) and still usable. But officially the SMTP stack is not supported.

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By: Cyril https://practical365.com/practical-exchange-understanding-smtp-relay-in-exchange-online/#comment-295347 Wed, 12 Jun 2024 06:45:04 +0000 https://practical365.com/?p=61004#comment-295347 Exchange Online to retire Basic auth for Client Submission (SMTP AUTH) in September 2025 :
https://techcommunity.microsoft.com/t5/exchange-team-blog/exchange-online-to-retire-basic-auth-for-client-submission-smtp/ba-p/4114750

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