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Email In Ventura 13.2.1 not forwarding attachments. Crashing when replying to emails with attachments

I have recently upgraded to Ventura. I am working on a Mac book pro M1 2020.


When I get emails with attachments such as documents or pictures, when forwarding them onto other email accounts it is not attaching the attachment.


If I "reply all" to any emails I receive it comes with a message "not downloaded content, continue? If I continue it crashes me out of my email account and fails to send the reply.


I am not having these issues on my iPhone mail.

MacBook Pro 13″, macOS 13.2

Posted on Apr 12, 2023 9:47 AM

Reply
Question marked as Top-ranking reply

Posted on Apr 12, 2023 9:53 AM

Give this a try: boot into Safe Mode according to How to use safe mode on your Mac and test to see if the problem persists. Reboot normally and test again.


NOTE 1: Safe Mode boot can take up to 3 - 5 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files


NOTE 2: if you have a wireless keyboard with rechargeable batteries connect it with its charging cable before booting into Safe Mode. This makes it act as a wired keyboard as will insure a successful boot into Safe Mode.


If that doesn't help Create and log into a new, basic, admin user account, Set up users, guests, and groups on Mac and see if the problem persists. This tells us if the problem is limited to your user account or is system wide.


Note:  do not launch any 3rd party apps in the account so as to not install any of the supporting files that most create.


If the problem isn't present then your original account has software installed that is causing the problem.  


1 reply
Question marked as Top-ranking reply

Apr 12, 2023 9:53 AM in response to dwbartonUK

Give this a try: boot into Safe Mode according to How to use safe mode on your Mac and test to see if the problem persists. Reboot normally and test again.


NOTE 1: Safe Mode boot can take up to 3 - 5 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files


NOTE 2: if you have a wireless keyboard with rechargeable batteries connect it with its charging cable before booting into Safe Mode. This makes it act as a wired keyboard as will insure a successful boot into Safe Mode.


If that doesn't help Create and log into a new, basic, admin user account, Set up users, guests, and groups on Mac and see if the problem persists. This tells us if the problem is limited to your user account or is system wide.


Note:  do not launch any 3rd party apps in the account so as to not install any of the supporting files that most create.


If the problem isn't present then your original account has software installed that is causing the problem.  


Email In Ventura 13.2.1 not forwarding attachments. Crashing when replying to emails with attachments

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