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I am a one-person business. I have a standalone system: high performance PC (bought in early 2021 from Puget Systems) with Microsoft Office Professional installed as part of the PC purchase. All good -- except in those instances when Microsoft goes through the back door at midnight and installs a Windows update... and messes something up. Right? Are you with me here folks?
I use Outlook 2019 (MS Office) because it's just a lot cleaner and has more of a spreadsheet/database look -- which allows me to be way more productive. Each message is on a single line. Compact and easy to read. Click on headers to sort quickly, etc. I am on Exchange (msn.com) and generally speaking it has been working fine. The web version of Outlook (and similarly the version my wife uses in the house... basic low-level/cheap-o Office 365 monthly subscription/rental) is visually more clunky.
A few months ago (maybe 6 months ago or more) all of a sudden I am looking at my Outlook 2019 UI -- and the little navigation toolbar that was in the bottom left corner by the Start button has now moved over on the left border, vertically. How and/or why did that happen? I didn't do it. Plus, I see a new little "flip switch" over on the upper right corner (by the minimize, maximize and "X" buttons) that says "Try the NEW Outlook" (or whatever it said). Again, I'm using Outlook 2019 (Microsoft Office). Initially I was not pleased that this change was made unilaterally by Microsoft (without asking) -- but you get used to it. After doing some research (MS Community) the reason was evident. We need to become "conditioned" to the new UI. OK, fine. Have it your way. The Microsoft Way.
So, this morning, I start working and need to send an e-mail. Outlook 2019 (MS Office). All of the folders look fine... Inbox, Sent Items, etc. All up to date. E-mail messages are being received. I compose the message. Again, I'm using the "Office" application (Outlook 2019). Click the SEND button... and viola! Outlook "crashes'' (we used to call that a GPF) and restarts. Hmmmm. Try again. Same thing. So, I delete my OST file and start Outlook 2019. It rebuilds the OST file (takes a minute or two since it was 1.9 GB before... and 1.5 GB after the rebuild). Try to send again. Crashes. Start Outlook in safe mode. Try to send. Crashes.
So... I go over to the Outlook web app, and yes indeed.... I can SEND an email. But when I check Sent Items to confirm (in the web app) the most recent message (Sent Items) is from 2020. The Sent Items folder (NEW Outlook) is not being updated. But the NEW Outlook Inbox is up-to-date. There's some sort of mismatch going on between Exchange and the NEW Outlook (web). Not good. When I go back to the "old" web application -- voila! The sent Items folder is up-to-date. GET YOUR ACT TOGETHER MICROSOFT.
So... I go back to Outlook 2019... and there too, the Sent Items folder is current (including the test message I sent via NEW Outlook). Again, something is goofed-up between Exchange and the NEW Outlook (web app) because the most recent message that I sent from the NEW Outlook is shown in "Sent Items" (Outlook 2019; being downloaded from Exchange to the OST file) and also on the old web version... but Sent Items in NEW Outlook is not being updated (the most recent message in the NEW Outlook Sent Items folder having a 2020 time stamp). Bozos! And now I'm also noticing (over in MS Office Outlook 2019) that the little navigation toolbar Microsoft unilaterally moved to the left border of the window... has now reverted back to the bottom left corner by the Start button. Plus, the little "flip switch" over on the upper right ("Try the New Outlook") -- or whatever it said... is now GONE (in Outlook 2019).
Sure, I can limp-by -- using the web version to send and then going back to Outlook 2019 to MANAGE my e-mails -- but what a PITA.
Microsoft "did something" to my system -- but who knows "What?" and who knows when this gets fixed.
Typical.
My guess is -- once I see Sent Items being properly updated in the NEW Outlook -- the issue will likely be resolved. Hopefully.
GET YOUR ACT TOGETHER MICROSOFT.
Using Classic Outlook on Windows for personal email, calendar, and contact management
Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.
Answer accepted by question author
Hi all,
The build with the fix just released Version 2311 Build 17029.20068, Outlook Desktop crashes sending an email from Outlook.com accounts - Microsoft Support. To install the fixed build, click File, Office Account, Update Options, Update Now.
Answer accepted by question author
It seems like the service change is taking a long time to be picked up by the client. My test client just picked up the change and the crash stopped but I still see a lot of reports for the issue.
I just posted a Known Issue article to formally document it, Outlook Desktop crashes sending an email Outlook.com accounts - Microsoft Support. If you still see the crash, you can use the steps I added in this article to revert to the prior working build.
What a relief!!!! Outlook 2019 (the legacy "Office" version) is SO MUCH FASTER and way more intuitive/flexible. Why can't the same functionality be incorporated into "New Outlook" (served application)?
Well, well, well. Why can't MS just be up-front and say it? There's no doubt that Microsoft (and a lot of other software vendors) really detest perpetual licenses. I get it. The software rental paradigm is where they all want to be -- as if MS isn't making enough money. For goodness sake. So, my guess is... that by intentionally going through the back door (midnight update) and hobbling Outlook 2019 (and... I suppose... eventually every other "office" version of Outlook) Microsoft can grab some low-hanging fruit and force "Office" people (perpetual licensees) to pay a monthly fee (either 365 Basic or 365 Personal). I'm guessing that Word and Excel are probably not far behind -- again, for single-user standalone perpetual license "MS Office" installations. And I'm sure there's verbiage somewhere in the massive MS Office EULA that allows MS to do this unilaterally. Pathetic. Just be straight-up and tell us what's happening. I am going to ride this out for the time being. Probably pay later. What turned the light on for me... since I've been "configuring" and fiddling with NEW Outlook for the past hour or two (since I need to SEND emails) is that my Inbox now has "ads" popping-up (which were "junk" before) and I cannot simply "highlight" and designate them as "junk" (as I could with Outlook 2019) nor can I highlight the message (benignly -- to "select" it) and DELETE the message. No! You are now forced to click on it -- which then opens up a browser window. Huh! Security? These "ads" have been vetted? On top of all this, I'm surprised they aren't forcing me to used Edge. Also, the "mark, flag, pin, delete" icons are situated on the right-hand side of a normal message... BUT... when it's an ad... they are situated in the "from" column (just to make it a little harder to evade the advertising). If you subscribe to 365 Basic or 365 Personal, then supposedly the "ads" go away. Supposedly! Until we're forced to pay again. So... MS has us coming and going. They are forcing us to pay to remove "ads" and I'm sure they are sucking money from the advertisers by allowing a select few who pay the real big bucks to get through some sort of AI-managed junk mail gate... in order to appear in our Inbox. Whereas... those who don't "pay" end up going to the junk folder. It's not that hard to figure out, is it? It would be funny if it wasn't so pathetic. Although I do buy Microsoft's office/business software, I'll admit that I've used "msn.com" as my email address (along with Outlook) for free... for almost 30 years. So in some respects, I suppose it's about time. But I'd prefer direct communication and transparency... a straight-up business approach... where Microsoft tells me what they are going to do -- and that way I can plan ahead and not waste half a day trying to figure out if I'm dealing with a bona fide "technical problem" -- or a PROBLEM BY DESIGN.
Doing a little more poking around... I stand corrected. Sent Items in the NEW Outlook is indeed up-to-date. I hadn't toggled the header -- because I never had to in the other apps (i.e., "old" Outlook web and, most importantly, MS Office Outlook 2019) -- since the most recent entry is always at the top. So... this probably puts me farther behind the 8-ball in terms of getting back to the way things were. I really like Outlook 2019 (MS Office). But it seems like this is probably another instance of "selective degradation of functionality" that Microsoft subtly employs... in order to eventually force us to migrate... and eat what they have to offer. Although not being able to SEND an message (without the program crashing) is a pretty significant cut in terms of application functionality... considering this is an e-mail application.