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Can't send email with attachments from Outlook for Mac desktop version, with Office 365 subscription. Get 'Message could not be saved' dialog Get 'Message could not be saved' dialog box. Attachment is not open elsewhere, permissions for file are set to Read/Write for current user.

Lately I've been having a lot of issues attaching files (jpgs, pdfs, etc) in Outlook. This isn't consistent, but often when I compose an email, then go to attach a file, it says it can't save the file with the attachment, and that I need to remove it. Needless to say it won't let me send the file with the attachment. The only workaround I've found is to restart my Mac - then it works for a while. Also, I'm having issues downloading attachments from emails to my computer. Often nothing happens – I've tried every way to save an attachment from an email - then I restart the Mac and it works. Sometimes I have to do this a few times a day.

Then yesterday I received a Word doc attachment, and couldn't open it - it said I didn't have the right permissions. When I go to Get Info, it says I own it.

I can open the same file today after restarting my Mac. This has happened a few times lately. I've rebuilt the permissions on my Mac, but that doesn't seem to help. I've been using Office forever. This is an issue that's been happening for a couple of months, and seems to be getting worse. MacBook Pro - 15 inch, 2016 macOS Sierra Office 365, all up to date. Hi Shelleroo, Thanks for your updates.

I mentioned that you had reinstall Office but the issue persists and you are also experiencing an issue that Outlook usually won't quit and you have to force it to. Given this situation, I suggest we first try following methods: 1. Please make sure your Mac OS is upgrade to the latest version. If the issue persists, please try to start your Mac in safe mode to see if this issue is caused by add-ins. If Outlook work well when you start Mac in safe mode, then you may check the add-ins you have used in your Mac. If the issue persists after you start your Mac in safe mode, you can try to create a new Mac profile and check the result.

Note: please backup your data before you create a new Mac profile. Here is an reference article:. Moreover, about the issue that you cannot send emails with attachments, if the issue persists when you try above methods, then this issue is related to Outlook for Mac client. To better help you, we highly recommend you to contact our dedicated Outlook for Mac team to get targeted help. Your time and understanding will be highly appreciated. Regards, Jennifer.