Win11 built-in New Outlook STILL can't handle a basic 'Send as Attachment' from MS Word - how is this acceptable in 2025? MAPI failure due to an "unspecified comedy"
Posted by caprazli@reddit | sysadmin | View on Reddit | 123 comments
Microsoft owns Windows. Microsoft owns Word. Microsoft owns Outlook.
Their own products can't talk to each other.
The "fix"? Save file, open New Outlook, manually attach like it's 1995.
Classic Outlook? Works perfectly. But Windows keeps pushing this broken "upgrade."
Found threads from 2023 complaining about this. It's 2025. Still broken.
$3 trillion company can't implement email attachments in their email app.
Anyone else tired of this comedy?
Muted-Part3399@reddit
Microsoft is a small indie company. You can't demand these types of things.
Everyone knows the real solution is to push everything to the cloud and share it using onedrive.
HotTakes4HotCakes@reddit
Unironically, this is what they want you to do.
Pretty much every decision they've been making with 365 is an attempt to train users to think of the Office suite as a web app, with begrudging exceptions for Excel.
Sinsilenc@reddit
I mean we use autosave with 2 different vendors. Its actually not vendor locked to one drive at all... If you go to account add a service then storage. You can see all the vendors it supports.
Glass_Call982@reddit
But why can't I auto save to my desktop or network share?? I'm pretty sure this used to exist before.
Sinsilenc@reddit
I dont think it ever has.
BasicallyFake@reddit
you cant expect anyone to rtfm
cdoublejj@reddit
well i'm moving to Germany where the government is pushing to switch to open source, at least when technology will fuck me it will be in the name of the proletariat.
Walbabyesser@reddit
The government -talks- about -maybe considering- alternatives. Don‘t be to overexcited about it
cdoublejj@reddit
Germany actually committed switching again a year or two or three ago
turmacar@reddit
I have to assume that when looking for a fix the average git contributor is both easier to contact and more likely to be bribable with beer than the average Microsoft Employee.
Jaereth@reddit
If talking about just MS support and not "employee" the guy on git probably has a more extensive background in tech as well :D
dispatch00@reddit
Absolutely the most fucking infuriating part of this.
Edexote@reddit
You understood their strategy perfectly. If nothing leaves your browser, there's no need for "legacy" features.
Jaereth@reddit
I'm waiting for when you open a fresh powershell terminal and it says "Welcome to Copilot Terminal powered by Powershell!" and i'm just gonna retire then.
jlharper@reddit
New Outlook for Mac is feature rich and we’ve been using it in prod for over three years. It’s really not an issue, and I can only wonder why they made the legacy application available for so long when the new version has been an ideal, fully functional replacement for over three years.
SecUnit-Three@reddit
the technology just isn't there yet /s lol
walkalongtheriver@reddit
I mean, why would they care? Everyone here is going to recommend 365/Office no matter what so what impetus do they have to change?
tejanaqkilica@reddit
TIL You can send a document directly as attachment from within Word.
Gwigg_@reddit
Not quite. Today you learned that you used to be able to send a document directly from word but as new outlook is not mapi it now just sits in a mapi queue until ……. You open old outlook 🎉🎉🎉
ScannerBrightly@reddit
mapi isn't great, though, is it?
Gwigg_@reddit
Absolutely right. It's not a tool for today's world but the point is that New Outlook is being thrust upon us without sorting either the underlying architechture or in fact anything at all about how it works. Utter shite. It is also 100% a ransom machine. Microsoft blocks access or breaks? NO ACCEESS for any historical stuff. Nothing. Hope you have a backup of your mail accounts somewhere. I so hate this arghhhhhh
saagtand@reddit
I think New Outlook is basically a fancy web outlook. Requires Edge Webview 2 Runtime to function.
TheRogueMoose@reddit
That's because that's just all it is. All the "new" apps are just Edge with a skin.
Sporkfortuna@reddit
And tbh for a lot of things they work better
And for some really important stuff they just don't work at all.
laseralex@reddit
What does New Outlook do better than Outlook (Classic)?
I tried it for 2 or 3 days last year and hated everything about it.
rfc2549-withQOS@reddit
It can save all your passwords in microsoft's cloud, in case you forget them.
https://blog.runbox.com/2025/05/outlook-stores-email-in-microsoft-cloud-what-you-need-to-know/
laseralex@reddit
Neat! 🙄
Cloudraa@reddit
its a lot better now than it was last year tbh, still pretty crappy but i find it runs a lot better, and the lack of anything stored locally stops weird .ost issues and having to rebuild profiles, etc.
personally i dislike it but i try and get people to use it as its much lower maintenance than classic outlook
laseralex@reddit
Does that mean it doesn't work without an internet connection? I often read and respond to emails on my laptop when I'm on a plane, and then sync when I'm in the hotel.
BasicallyFake@reddit
new outlook does have an offline function, it did not at launch
laseralex@reddit
Oh cool! I'll have to give it another stab.
Syphor@reddit
New Outlook is better these days than it used to be but lately I've been having issues with people getting corrupted PDF attachments only when using New Outlook. Might apply to other filetypes as well but these are the only reports I've gotten so far. Not sure if it's an encoding issue that New Outlook doesn't understand or something else.
The PDF can be successfully downloaded/extracted from both Web and Classic Outlook, but the file you get from New Outlook - and not all of them! - is just entirely wrong.
BasicallyFake@reddit
I think they actually admitted that bug and fixed it
Cloudraa@reddit
yup ive seen that as well, pretty sporadic though
Sinsilenc@reddit
It handles larger inboxes alot better for one thing.
Sporkfortuna@reddit
It's fast, it has a more seamless experience when using other 365 apps. From a strictly selfish standpoint I love that it's close enough to the web version that my users aren't asking for license upgrades if they're used to it. To be honest I haven't used it much myself either because I still work with the features it doesn't yet have, but for the things it DOES do, I think it's a pretty nice app.
QuesoMeHungry@reddit
This is the problem. Microsoft is trying to move all of the office apps to web views wrapped in edge. No more ‘native’ applications.
Froggypwns@reddit
I've had users that for whatever reason open their browser and go to webmail instead of the fat client on their main terminal, then call the Helpdesk to report their attachments they were trying to send with the send as attachment function were not sending. The second I open the full client to check on it, the dozen items in the outbox send.
Atrium-Complex@reddit
No shit, had this exact thing happen, and then like 3 weeks of reports suddenly spammed out from a users mailbox the moment we switched it back to old outlook... blasted like 200 emails to people all at once.
Darkhexical@reddit
You can sort of. Works with share when right clicking the document. I haven't tried outside of that though.
MairusuPawa@reddit
Years ago, this actually fucked up all email standards and made life hell for people not using Microsoft products.
ddejw@reddit
Can you expand on that please?
zvii@reddit
Right? This has never been in my flow. Go to the app I want and attach file.
Lv_InSaNe_vL@reddit
You can right click on any file in your file explorer and send it as an attachment right from the context menu too!
Well, you used to be able to. As with most things it doesn't work with new outlook.
xCharg@reddit
No you can't, gotcha :D
burnte@reddit
It's pretty bad. New Outlook gets uninstalled on all new machines for me.
jake04-20@reddit
Can't you just not include it in your corporate images?
burnte@reddit
Images haven't been license compatible in a long time, these days most companies use scripting to create compliant machine environments. We drop ship right from CDW to the user, they sign in and it's all set up automatically via Intune and Autopilot.
jake04-20@reddit
What do you mean by license compatible?
burnte@reddit
Making master images you flash to multiple PCs violates the EULA and has for a while unless you do it correctly with sysprep and all that.
jake04-20@reddit
AFAIK you need a volume license agreement. But why wouldn't you do it with sysprep?
RyeonToast@reddit
The only group MS hates more than sysadmins are users.
RJBusta@reddit
Comment of the year
HotTakes4HotCakes@reddit
They're trying to push you to use the web app version of Word, where it will work.
Pretty much every decision they're making can be summed up as we really want the customers to stop thinking of office as desktop software, and something that only lives in Edge.
ComeAndGetYourPug@reddit
"Oh that's great, everything works on an iPad now so I don't have to buy a PC anymore!"
Microsoft: "..."
Arudinne@reddit
Accounting will still need Excel regardless of the device they are using.
per08@reddit
Still there. But instead of the VB Macro of doom, Microsoft is pretty much doing all they can to get legacy workflows out of spreadsheets and into Power Apps.
AP_ILS@reddit
I really don't think they care if you are using Windows as long as you are paying to use their cloud services.
CEONoMore@reddit
They are killing windows explorer.
THE application that is the top reason anyone preferred windows for a long time, is being butchered by Microsoft
Notice how slow it has been getting with OneDrive integrations ?
Also what’s up with the UI locking and not responding when clicking on a network unit that is offline? That one seems to be old bug though.
For me, also calendar was broken yesterday. There’s a horizontal line marking what time is it now which was not updating yesterday it got stuck many times and wasn’t showing the correct time there or in alerts either.
I’m tired of being a beta tester. I’m waiting for Steam OS to move to Linux for my personal use
sexbox360@reddit
Ye the new windows explorer sucks ass. The old one from w10 is fast and amazing.
I couldnt care less about tabbed browsing.
WhatsFairIsFair@reddit
Windows Explorer and search has been shit since xp. Search was shit in xp too but at least it didn't have irrelevant web search results and ads littered into the UI
sexbox360@reddit
Really? I liked win 7s explorer. I could press windows E and it came up instantly
WhatsFairIsFair@reddit
Ok i never used win 7 tbh. I went ME, 2000, xp, 10, 11 (I think)
DarthPneumono@reddit
...Explorer was the reason anyone preferred Windows? What?
CEONoMore@reddit
At a user level. Mos def. Would you be willing to hear complains about “what is this nautilus file browser” from your 300 users org? Or where is my Document and Settings ? Or “why is there no C drive”?
I understand those are more about other components of the OS than the explorer, but I was trying to figure of speech represent that navigation of the OS, components, folders, settings…..
All those had been respecting some continued practices that made the product predictable and reliable
Well, not anymore….
DarthPneumono@reddit
I'd say alllll the line-of-business software like Office, Adobe, AutoCAD, etc. was a way, way bigger issue than the appearance of the file explorer.
Taur-e-Ndaedelos@reddit
That's beyond old - it's ancient at this point.
Back in the XP days it could even hard crash the file explorer and you'd be stuck with a black screen until a restart or if you had the wherewithal to Win+R and run explorer.exe. No auto restart of the explorer process back in ye olden days. Now get off my lawn.
olback_@reddit
A coworker had explorer crash yesterday without restarting. It usually does, but not always.
It's so funny to me as a software engineer that we still don't know how to do io-heavy things in a background thread. It's not even that hard to do correctly these days.
jake04-20@reddit
If a client machine has a network drive mapped, but can't connect to it (because the server is offline), our windows explorer just doesn't open at all. It will just freeze until that server comes back online and the drive can reconnect. This happens specifically on win11 clients, not win 10. But it also only happens on the corporate network.
carpetflyer@reddit
Notepad has gotten so slow. Original notepad was fast.
The new one with copilot bullshit even if I turn it off still takes a little time for the app to open because it has to render all the bullshit in the toolbar.
Original notepad had just a basic menu.
Fuck them
Bladelink@reddit
Fwiw gaming on Linux is basically solved now with Proton. I've been gaming on Linux since windows 11 was announced and I saw which way the shit was flowing. The only games that actually aren't supported are the ones with kernel level anticheat, which you shouldn't really want to play anyway since they essentially demand to install spyware on your computer. Everything on Steam just works, and most everything on Epic (which tbh I don't use anymore) works fine with Heroic launcher.
dnuohxof-2@reddit
Microsoft is exemplar of the Right Hand doesn’t know what the Left Hand is doing. Every product feels shoehorned into the windows system. Design language, cross app features and general productivity are all so half baked it’s not funny. They’re so concerned getting a product out the door they don’t feature complete it, they don’t QA it, they just send it and hope for the best.
graywolfman@reddit
They are so big and dysfunctional that the right pinky doesn't know what the right ring finger is doing. The right hand has never even seen the left hand, nor does it know that it exists.
boli99@reddit
https://ritholtz.com/wp-content/uploads/2013/07/2011.06.27_organizational_charts.png
SwatpvpTD@reddit
Oracle one is great.
Describes Oracle just perfectly, as I always hear about Oracle when someone is talking about licenses, never in an engineering context. Oracle Cloud is probably run by legal too, as it's been impossible for me to try to sign up to explore alternatives to Azure and AWS.
Raskuja46@reddit
It's getting to the point where I'm genuinely concerned about the future of the Windows operating system.
Jaereth@reddit
It isn't this. This is giving them too much of a break and too benevolent.
All of this is just to drive you into their new ways of doing business. This is just one of MANY things, even in Outlook alone, that is just "Oh switch to the new version" as the solution. They are very strategically and purposefully letting stuff like this slide.
imnotaero@reddit
Microsoft owns document cloud storage users pay for. Microsoft owns email networking and mailbox storage Microsoft pays for.
I understand the frustration with a feature that doesn't work, but I don't understand why people have trouble realizing that this is an expression of Microsoft's priorities. They don't want you attaching documents to email.
You can always try to swim upstream against the flow of your providers' intent, but it's going to take more energy. Wisdom is knowing when to change direction. (Note: I'm not so wise, myself.)
pdp10@reddit
If they hadn't been a few decades too late, we could have been on the same side.
Cry_Wolff@reddit
They are a bunch of dumb fucking assholes then.
caprazli@reddit (OP)
The users are the stream
EquipLordBritish@reddit
It's 2025. Most software ships with major bugs now.
ccsrpsw@reddit
"Send As" attachment from Word is an abomination. It should never have existed, and should really be removed.
But Im also a curmudgeon who would like to take any and all people still printing spreadsheets on a small trip out to a dark corner of the parking lot to explain why its a bad idea to print that 34x20 maze of sheets several times because you forgot the order :)
Lurk3rAtTheThreshold@reddit
New outlook started sending me toast notifications even though I'm still using classic. If I click on the wrong notification, it opens new outlook and doesn't even open the message from the notification...
iamnewhere_vie@reddit
Solution :D
Remove-AppxProvisionedPackage -AllUsers -Online -PackageName (Get-AppxPackage Microsoft.OutlookForWindows).PackageFullName
DramaticErraticism@reddit
I appreciate that there are very good technical reasons for why these features don't exist and are hard to create.
With that being said, we don't want a product to replace a perfect product with 20+ years of development. We want old Outlook and old Outlook was great.
They are creating a problem and trying to build a solution for it, when they already have the solution.
cccanterbury@reddit
it's more a tragedy at this point.
unccvince@reddit
Perhaps with all that cloud stuff, I will invest in computer mice manufacturers, because the number of clics is going to skyrocket and create this new exciting market of Mice as a Service.
Edexote@reddit
You seem to think this isn't a feature. You don't need that if you use cloud based apps stored on OneDrive/Sharepoint/Teams. Get it?
adx931@reddit
Working software doesn't sell subscriptions to services that fix the deficiencies they intentionally added to the desktop product.
flummox1234@reddit
but it has AI!
wideace99@reddit
Stop complaining !
Since you accepted to be vendor lock-in your opinions means nothing, just keep paying :)
YetAnotherSysadmin58@reddit
It deps love buying vendor-locked products then whining when they suck and can't interop or leave, it's in our blood.
Bladelink@reddit
In my experience, us Linux support people are forever leery of vendors.
hyperflare@reddit
Yeah, because we can actually fix things ourselves. Most Windows Admins are just button pushers who need a never-available "support" to shift blame to when things don't work.
whatdoido8383@reddit
Yep, the integration between Outlook and their file sharing solutions is absolute garbage. Why I still can't attach a file from SharePoint\Teams in the new client blows my\my users mind(s).
kearkan@reddit
My favourite part is where they had copilot in outlook starting to get to the point where it could interact with all settings (great since nothing was anywhere that made any sense). Then they just... Got rid of it... And now it's just the same as what's in edge and it's back to giving (out of date) instructions.
Ron-Swanson-Mustache@reddit
How Microsoft's different dev teams interact
ryanlaghost@reddit
lol and we are upgrading to win 11 in about 2 months.
ohyeahwell@reddit
MAPI doesn't work with new outlook at all. Same issue with Bluebeam.
compu85@reddit
Welcome to the new standards for software. Why test when the users can do it for us?
green_link@reddit
New? This practice of having the consumer test your software has been around for a couple of decades at this point. Once distribution and updates were switched to being online and distributed via the internet that's when development went 'the end user can test for us'. Why test in house when you can push the new version/update and fix it later? That was some god damned middle management decision.
Wulf621@reddit
It's working as intended. Instead of paying to use their cloud, host your own
SirHerald@reddit
I did it the other day. User was in New Outlook but word was sending to old Outlook and it wouldn't send until I activated old Outlook.
The fix was changing Outlook to classic and then back to New. There was a setting in office that just expected sending through classic until you explicitly set it.
N0b0dy_Kn0w5_M3@reddit
Why in the fuck would you then continue to use New? Just use Classic.
SirHerald@reddit
Not my computer.
But then I have my main work computer on classic, and my laptop on new so that I have experience with both. I have to support other people's systems
mrh01l4wood88@reddit
It's acceptable because you accept it and still give them money for their crap products.
The best time to learn Linux is last decade. The second best time is today.
zeno0771@reddit
The C-suite and IT don't want the same thing, and the decision-making between the two only flows one way. We're not sales reps, we're the people who mop up after the sales reps enable the bean-counters.
Besides, Red Hat/IBM aren't exactly a shining example of "we're all in this together"-type thinking these days.
ExceptionEX@reddit
I don't know why people are so quick to try to move to beta software, until I see a compelling reason to move to their new inferior product, I stay on the old version of outlook.
D0nk3ypunc4@reddit
New Outlook isn't ready for primetime. Just block it across the board.
This is the way.
https://learn.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/outlook-on-the-web/enable-disable-employee-access-new-outlook
droog62@reddit
This is why Outlook "Classic" is still going to be supported for 4 more years. It's a steaming pile of let's shoehorn everything into the cloud till people forget how things used to work.
Chubakazavr@reddit
Microsoft will continue release even more shittier products over the years because us, consumers, continue to pay for it. we vote with our wallets basically.
catwiesel@reddit
its a glorified webapp, or at least, its going to be. integration? with existing API? well. if it works, okay, if not. tough luck. and why would, should they fix it? people will continue to use, and pay for broken shit anyway.
unless people start looking at you like you eat chrildren when you utter the word thunderbird or open/libre office, microsoft has not even a reason to consider listening to the customers
ledow@reddit
Hehe, wait until you try to send things with Teams from the official app on an Android phone, etc.
I have sometimes also literally been told "You can't send this attachment, it's too large to share using Outlook, use Onedrive instead" and when you go to do that you get an entirely different error saying to send its too big and to send via email using Outlook instead:
binarycow@reddit
The error on the left doesnt say to upload it to one drive. It says to put it in a "shared location". There are other shared locations that support larger file sizes.
dotdickyexe@reddit
Its crazy been through this and drives me nuts.
Practical-March-6989@reddit
We cannot use the new outlook because our exchange account is not compatible. Muppets.
Extension-Ant-8@reddit
Outlook Classic is supported until Q2 2029. Stop using that shit. Stop beta testing a paid product. Just because they call one new and one classi. Doesn’t mean. You migrate. Test. Sure, but it’s not feature complete. Disable that shit, and Test 4 years from now instead.
bingle-cowabungle@reddit
They don't want you to do that. They want you to save it to OneDrive/Sharepoint and share it that way.
peachyteasess@reddit
Been there. ‘Send as Attachment’ from Word? Might as well hand deliver it via carrier pigeon lol.
Igot1forya@reddit
XanII@reddit
'Failed successfully!'
Win11: Are you not proud of me?
saagtand@reddit
The same phenomena occurs if you try to attach a file via file explorer. It will open Outlook Classic instead. ;)