Messages app unable to send photos over iMessage from iMac OS 10.15 Catalina

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Level 1

4 points

Messages app unable to send photos over iMessage from iMac OS 10.15 Catalina

When I try to send a photo to someone in Messages by dragging and dropping an image, the progress bar never reaches 100%. And eventually I get a red exclamation mark next to the image saying the message failed to deliver.

I have reset the NVRAM, signed out of iCloud account in messages, deleted the .db files from the Library>Messages folder, restarted the computer, Disabled messages in iCloud

None of these seem to have resolved the issue. Has anyone else experienced this and managed to get this resolved?

iMac Line (2012 and Later)

Posted on Sep 3, 2020 10:37 AM

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Answer 1

Best reply

Eric Root

Level 10

684,057 points

Sep 3, 2020 10:47 AM in response to yash Gupta

Are you running any anti - virus programs? Using a VPN?

Try setting up another admin user account in System Preferences/Users & Groups to see if the same problem continues. Also try the Safe Mode.

Isolating an issue by using another user account

Safe Mode - About.

If it works in the Safe Mode, try running this program when booted normally and then copy and paste the output in a reply. The program was created by Etresoft, a frequent contributor. Please use copy and paste as screen shots can be hard to read. Click “Share Report” button in the toolbar, select “Copy to Clipboard” and then paste into a reply. This will show what is running on your computer. No personal information is shown. If the log won’t post, try posting it in Pastebin and provide a link in a reply. After pasting the report in a PasteBin page, go to the top of the page, and copy the address in the URL bar. Paste that in a new reply. Pastebin.

Etrecheck – System Information.

Web site version if required. https://etrecheck.com

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Answer 2

yash Gupta Author

Level 1

4 points

Sep 3, 2020 10:54 AM in response to Eric Root

Thanks,

I don't believe I have ever installed any anti-virus program on this Mac. And no VPN either.

My connectivity is via ethernet for fast speed and wifi for airdrop and continuity/handoff.

But here's a big update on the situation:

Copy and paste worked for a file from within my "Pictures" folder. Then I tried drag and drop and it worked for the file from that folder too. Turns out the files from my external hard drive and its photos folder won't go through with copy and paste or drag and drop(which is what I had been trying up until now) However, if I copy an image from external drive>photos to the User>Pictures folder first, and then try to send it, the photo goes through.

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Messages app unable to send photos over iMessage from iMac OS 10.15 Catalina

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