Long file names of attachments might be shortened in Outlook Web App. A shorter name doesn't affect the contents of the file. Creative cloud app installer not working mac os. Depending on the service that’s hosting your mailbox, the default size limit in Outlook Web App for an entire message, including all attachments, is 25 MB or 35 MB. In the Mail app on your Mac, do any of the following: Click the Attach button in the toolbar, locate a file (you may need to click the sidebar button to see additional folders), select it, then click Choose File. You can also drag files from the desktop, the Finder, or an app into your message.
I frequently use the drag & drop method to add an attachment to an email directly from Explorer rather than using the Attach File button.
However, as of recently, this method no longer works for me. When I try, the cursor turns into some sort of a forbidden/blocked/unavailable sign.
Is there any way I can reinstate the “drag & drop to attach” feature again? Stopping apps from automatically starting on mac.
There are 2 common situations in which the drag & drop feature breaks but luckily, reinstating it in either situation is very easy.
Esc, Esc, Esc
If dragging and dropping items suddenly has become unavailable to you throughout Windows (so not just Outlook), try hitting the Esc button on your keyboard a couple of times. Hitting it 3 or 4 times usually is enough to get drag & drop to work again.
I’m not sure of the root cause issue of this one but it only happened a handful of times to me over the last couple of years. Rebooting does the trick as well but that might not always be a direct option. The old habit of repeatedly pressing the Escape button actually came in useful this time.
Outlook is running with administrator permissions
Another situation in which the drag & drop feature breaks, is when Outlook has been started with elevated permissions. Or to put it in other words; it is running as an administrator.
![Cannot Attach File In Outlook Web App On Mac Cannot Attach File In Outlook Web App On Mac](/uploads/1/3/4/1/134155353/725988734.png)
As you are then running Outlook with different permissions than Explorer, drag & drop between the two won’t work. When you try, the cursor will turn into this blocked sign as soon as you hover with your attachment over your Outlook message rather than turning into a “move or copy selection” pointer.
Dragging & dropping attachments won’t work when Outlook runs as an administrator. (click on image to enlarge)
Reasons for this to happen is that somehow compatibility settings were enabled for your Outlook shortcut or you held both CTRL and SHIFT while starting Outlook.
When Outlook is started like this, Windows usually then also prompts you with an User Account Control warning; “Do you want to allow the following program to make changes to this computer?”
To solve this, hold the SHIFT button when right clicking on your Outlook shortcut in the Task Bar (Outlook should be closed) and choose Properties. Then, select the Compatibility tab and make sure all selections are turned off.
![Cannot Attach File In Outlook Web App On Mac Cannot Attach File In Outlook Web App On Mac](/uploads/1/3/4/1/134155353/690700389.jpg)
Most likely, the option “Run this program as an administrator” is selected for you.
Cannot Attach File In Outlook Web App On Mac Shortcut
Make sure no Compatibility settings are set for Outlook. Accidentally deleted safari app on mac.