Outlook.com is silently discarding email messages (2015)

We, an online store, have found deliverability to yahoo.com and btinternet.com addresses by far the worst, I don’t have statistics to hand but it’s up to a 10% failure rate. Much like the OP it seems to be silent too. We have literally no issues with other providers.<p>The unfortunate thing is that we also find the demographic of customers here in the UK still using btinternet.com email closely aligns with customers who tend to be more problematic…<p>(My parents have a btinternet.com email address)

Trying to get detailed logs from Outlook365 hosted accounts is near impossible.<p>You&#x27;d think you&#x27;d be able to log in to your Exchange dashboard and just look at them. They hide it from you and only show you abbreviated logs. You can go through support, and if you pay enough money you&#x27;ll get an cryptic answer within a week (if you&#x27;re really lucky the support person might show you the real logs).<p>Pain in the ass when you&#x27;re trying to figure out why your users aren&#x27;t getting email from someone.<p>You can pry the mail logs from my cold dead hands.

I really don’t care anymore if my email reaches Outlook or Hotmail addresses. It’s impossible to make sure. And to some extent it’s also the users problem.<p>With Office 365 I have far less issues. So Microsoft can do it, if they want to.

This is fairly normal in today’s world of email providers, and one of the reasons it can be painful to manage your own SMTP server, right?<p>Mail delivery is an anarchy and I’m impressed the problem of spam has been solved to the degree we currently see. Yes it’s much more centralized than before, and no that isn’t a good thing, but from a customer’s experience point of view, I couldn’t go back to the old days of manually training your email client’s spam filter and whatnot.

In the end it is Microsoft&#x27;s problem, since they are the ones that are losing valid SMTP traffic. If a sufficient amount of users are experiencing a loss of e-mail as a result, then they will be forced to fix it.<p>There is almost never any valid reason to block an entire ip address. Single user accounts (e-mail addresses), maybe, if compromised.<p>E-mail, as a standard, is still pretty straight forward. Ideally you should be able to send e-mail directly from your laptop IP, if approved to send e-mail on behalf of your e-mail account &#x2F; host name. Decentralization is important.

Barracuda ESS appears to block everything from Amazon SES even with valid DKIM and SPF. Of course they can’t be bothered with DMARC reports. This really sucks for users trying to receive Cognito password reset emails.

I had same problem with deliverability of emails to Hotmail accounts a few years ago, they blocked AWS SNS IP email servers so sometimes were received but most of them directly sent to SPAM or never received. We complained Microsoft and their solution was to use one of their cloud email service or partner because the &quot;black magic&quot; of their AI filter. This is a shame

I worked at MS during the launch of outlook.com, got some good email addresses without numbers on it, and used them for years. This and other issues caused me to give up and change to a different provided within the last few months.<p>The Outlook teams are weird. They all have their own special feedback mechanisms that are different from the rest of Office, and they for the most part ignore them.<p>Earlier this year, for some reason the SMTP servers were changed from smtp.live.com to smtp.office365.com, breaking a number of my workflows and integration with other tools. This is meaningless pain that served no point - you could just point the DNS records for smtp.live.com to the exact same servers smtp.office365.com points to. Combined with other things Microsoft has done (breaking decades of links to MSDN blogs and support pages without providing redirects) I have no faith in the stability of the product in the future.<p>Their web view generally sucks. It doesn&#x27;t play nicely with the back button - selections are lost, search results are bypassed. It gets randomly stuck where it won&#x27;t load or will load the wrong CSS for hours at a time on multiple of my machines.<p>The Android and iOS apps have largely not changed since they used to be Accompli. I can&#x27;t name a new feature in the last decade.<p>Why, in the left nav bar, is there an icon with an envelope and a plus button that is &quot;connect a GMail account&quot;? That icon suggests &quot;write a new mail&quot;, which is a function I would do quite often. I never want to connect a GMail account - much less have it take up a dedicated button that&#x27;s always present in the UI.<p>Outlook on Android has its section buttons (mail, calendar, etc.) on the bottom. Mail for Windows has them on the bottom. Outlook 2016 and 2019 have them in the lower left. Outlook.com for many years had them in the lower left (if vertical). At some point they&#x27;ve moved to the upper-left, which is inconsistent with every other Microsoft-provided way that I check my mail and a regular source of frustration when I throw my mouse and eyes to the lower left corner and find nothing there.<p>I could go on and on (my favorite bug is that they removed the Send Feedback button that their docs refer to so I can&#x27;t tell them any of this). I was an Outlook fan for several years, but I could have written most of this feedback in 2015 and nothing&#x27;s changed; at this point I would encourage anyone still using it to just forward their mail to some other provider and be done with it.

I have another strange issue.<p>The document attachments which come along with incoming email are still listed in &quot;Documents&quot; tab in Outlook even after they have been purged from secondary trash. The documents themselves aren&#x27;t available (cannot be opened) but a list of all documents which have ever arrived (including JPGs&#x2F;PNGs in signaturss) are still visible in that tab. I flagged this issue once but no resolution yet

I think at least part of the solution should be replying to all such instances with &quot;Hello your client is broken. Would you mind using a different client.&quot;<p>It&#x27;s a ridiculous and easily dismissible statement at first, but not so ridiculous if it becomes commonplace&#x2F;familiar&#x2F;canon (it worked for internet explorer!)

Another one to watch out for is Gmail silently truncated emails (if the unsubscribe button is missing, often it is in the truncated part). You can&#x27;t get to the missing parts easy on mobile I think.

I get a lot of false positive in my spam folder when using Microsoft&#x27;s email service.