Mail app not sending emails with attachments on Ventura and IOS!

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Mail app not sending emails with attachments on Ventura and IOS!

This is a weird problem. The mail app on ALL my Apple devices will not send emails if there's an attachment with the mail. The email just sits there in the outbox and eventually, I'll get a message asking if I want to try from a different account. I choose a different account and the same thing happens. Eventually the email may go but usually I just keep clicking 'try another account'.

The strange thing is that this also happens on my iPad mail app too.

If I download another Mail app on my Mac - I tried the outlook app, there's no issue. The mail is sent almost immediately.

If I go to the web interface of Outlook.com (my main email address), mail is sent immediately.

I would use the Outlook app but for some reason, it won't allow me to setup my iCloud email accounts..

Can anyone suggest anything?

MacBook Pro Apple Silicon

Posted on Feb 15, 2023 9:30 AM

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Answer 1

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Randall_2023

Level 5

4,243 points

Feb 15, 2023 3:45 PM in response to SpongeBlob

What version of Ventura are you using? If not the most recent of 13.2.1, you might want to upgrade and test again. And/or, reboot into safemode which runs system diagnostics and repairs problems found: (Also while in safemod, try sending emails again to see if they work)

Start up your Mac in safe mode - Apple Support

Also for testing purposes, if you are using any 3rd party utilities like CleanMyMac, or Anti-Virus, or VPN software, you should remove those, IF your mail sends correctly while in safemode, it means another 3rd party application is interfering with your Apple Mail application.

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Mail app not sending emails with attachments on Ventura and IOS!

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