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Outlook Webmail not allowing attachments with Safari 14.0.1

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neutrino23

macrumors 68000
Original poster
Feb 14, 2003
1,881
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SF Bay area
I use Outlook Webmail in Safari a lot on MacOS. This has worked OK for years. Today I found that with Safari 14.0.1 I can't attach a file to an email. When I select Attach / Browse This Computer nothing happens. No error, nothing. I've tried restarting Safari. I've looked at permissions for this website and they are wide open. Is anyone else seeing this? Any suggestions?

If I select Attach / Browse cloud locations this works. It brings up our corporate One Drive account. It also presents me with some suggested files to attach from recent attachments. It just won't let me browse to select a new attachment.

This is on a 2019 iMac running Mojave. 10.14.6

Thanks.

Edit: Now I've noticed that when I tried to upload to Dropbox that also does nothing. I click the button to upload and nothing happens. I can drag a file to the window and it uploads OK. Maybe this is related? Anyone else seeing issues with Safari?

If I wanted to delete and reinstall Safari, how do I do that?
 
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neutrino23 said:
I use Outlook Webmail in Safari a lot on MacOS. This has worked OK for years. Today I found that with Safari 14.0.1 I can't attach a file to an email. When I select Attach / Browse This Computer nothing happens. No error, nothing. I've tried restarting Safari. I've looked at permissions for this website and they are wide open. Is anyone else seeing this? Any suggestions?

If I select Attach / Browse cloud locations this works. It brings up our corporate One Drive account. It also presents me with some suggested files to attach from recent attachments. It just won't let me browse to select a new attachment.

This is on a 2019 iMac running Mojave. 10.14.6

Thanks.

Edit: Now I've noticed that when I tried to upload to Dropbox that also does nothing. I click the button to upload and nothing happens. I can drag a file to the window and it uploads OK. Maybe this is related? Anyone else seeing issues with Safari?

If I wanted to delete and reinstall Safari, how do I do that?
Click to expand...
Just searching the internet about this. I have the same problem with browsing for a file to attach. If I click "Attach" and then "Browse this computer" it does nothing. "Browse Cloud Locations" works ok. I always use Browse this computer though. Dragging the file to the message works as well.
 
Wow I finally found somebody having the same exact problem. I searched everywhere and couldn't find any help. I tried opening Outlook Mail in Firefox......guess what? I can add attachments there just like I used to do on Outlook Safari. What the heck happened here. Does anybody have an answer?
 
I have the same problem, Late 2013 iMac, Mojave 10.14.6 and Safari 14.01. Started after most recent Safari update. I use Cox email as well as Google. I can work around by dragging attachments into the body of the email. Things seem to be ok when using Apple Mail or the Chrome browser with both Cox and Gmail. All of these work arounds for what should be a stable system is getting old. You are pressured to update for the latest security features but other problems result. Not always a good user experience with Apple.
 
Same exact here. I talked to Apple care and he was dumbfounded....again tried to get me to update. He dis show me that I can go to finder and select while trying to attach to email and they will all be there. I told him he now has something to work on in his spare time. Hopefully, apple will come up with an update to fix. Grrrr I hate to see that message "Update" waiting.
 
Yup, Safari 14.0 doesn't allow you to browse your computer for files in any web application such as Outlook Webmail when running Mojave 10.14.6 - please sort this soon Apple. My daughter was in a panic because her university portal doesn't allow her to drag files from the desktop and she needed to upload an essay. So annoying when upgrades add new features you'll never use but disable something you use regularly. In the meantime, use Chrome or Firefox as your browser.
 
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I have a lot of complaints about APPLE software issues like these (and many others) so ive made an automated script that sends 4000 form submissions per day on their website. ive set it up to flood them with reports about this particular bug. hopefully well see some progress. if anyone wants me to share it so you can let them know as well too let me know. (also discussed here)
 
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neutrino23 said:
If I wanted to delete and reinstall Safari, how do I do that?
Click to expand...
I've been searching for an answer. unfortunately I cannot find one. seems like the only way would be to reinstall macOS entirely or (better) to restore to a Time Machine backup before you installed 14.0.1. Im going to try manually copying an older version of Safari to my computer from Time Machine but I don't know if it'll work. stand by

EDIT: does not appear it can be done, I tried deleting Safari 14.0.1 using Terminal and replacing it with Safari 14.0. It not only broke some of the UI (tab outlines would not show up, for example), but the "file upload" bug still remains on all websites. I even tried replacing some of the Library > Application Support > Safari files and the Library > Containers > Safari files but no luck
 
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I wouldn't go to the bother of reinstalling Safari, especially if it involves reinstalling the entire macOS. I would wait for a fix from Apple and in the meantime, use an alternative browser such as Chrome or Firefox.
 
UPDATE: one temporary solution I have found is to drag and drop the file you want uploaded ONTO THE "Upload File" button if there is one. that effectively uploads the file. A little less convenient but it works
 
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Same problem. Contacted Apple Care who went through process for re-downloading Mojav. This enabled me to attach files for a day or so and now attachments have stopped working, again. Is it something to do with the recent security update?
 
Just joining the thread as I've got this problem too. Been using Outlook through a web browser for years with very few issues and the day after doing the latest update I'm unable to attach files. Very frustrating. Hoping it will get sorted soon.
 
Is anyone else experiencing this issue with the Media Browser's Photos section? I have iCloud Photos enabled and they are downloaded to my Mac, but no images ever load.
 
stevejobswouldbesad said:
UPDATE: one temporary solution I have found is to drag and drop the file you want uploaded ONTO THE "Upload File" button if there is one. that effectively uploads the file. A little less convenient but it works
Click to expand...
Thanks for pointing this out. I have just tried it and it does work.
It's actually a better solution than clicking the paperclip (attachment) symbol and trying to navigate via "Browse this computer". I open a Finder window where the file is located; click and drag the file I want to attach over to the message area of the new email I am writing; the message box lights up with a "Drop Files Here". And job done.
 
I have the same problem. Started this week. I can't attach anything from "browse my computer"....nothing happens.
 
I would add that the inability to "browse computer" to attach a file occurs on other websites for me besides Outlook. Is it specific to Safari 14.0.1 and certain version of MacOS (I am on 10.14.6)? I have accessed these same websites on my iPad or using a different browser (Vivaldi) and these do not have this problem. So as far as I can tell, it's seems to be specific to Safari (+/- certain MacOS version).
 
I am having the same issue. I am also a student and have to now use Chrome to submit any assignments on Canvas as well as attaching documents on Outlook mail.
 
Apple literally just released Safari 14.0.2 for Mojave and guess what? FILE UPLOAD IS STILL BROKEN. MacRumors' functionality works, which is weird, but any other site that has a normal "choose file" button doesn't work:

See on https://ps.uci.edu/~franklin/doc/file_upload.html or https://viljamis.com/filetest/ (websites you can test basic browser file upload capabilities)

EDIT: If you download the macOS Mojave Installer from the App Store and install it over your current build, it'll re-install Safari 14.0 and you can choose to ignore the 14.0.x updates after.
 
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