IMAC mail not allowing sending of messages

Watercolor123 wrote:

I put on "undo send" for 10 seconds and went to the scheduling and said "send now" I have never had scheduling on... but still not sending mail

Given the "Undo send" being off causes MAIL to CRASH - I think there is a bad MAIL app on the imac or it is corrupted or something like that.

You can launch the Mail.app holding the Shift key down and try again.

If an app freezes or quits unexpectedly on Mac - Apple Support

Mail.app is baked into the macOS there is no stand alone mail.app you would re-install the macOS to refresh the baked in apps.

Uninstall  all third party apps that are Cleaners/Optimizers/Anti-Virus/VPN

all known to cause issues on the macOS

ref: reinstall the macOS on top of your existing macOS

How to reinstall macOS - Apple Support

To trouble shoot further you can:

 —A SafeBoot Use safe mode on your Mac - Apple Support will sort many anomalies

Does a quick disk repair before it fully boots up, and certain system caches get cleared and rebuilt, third party system modifications and system accelerations are disabled.

Login and test. Reboot  as normal and test.  Caches get rebuilt automatically.

This test will tell you if third party interference; most* extensions etc are not loaded in safe boot mode. 

—Test issue in another user (or guest user) account Change Users & Groups settings on Mac - Apple Support

  This will tell you if it a universal issue or isolated to your user/admin account. 

no insight or resolve—

Call Customer Support  (800) MY–APPLE (800–692–7753)

or on line  https://getsupport.apple.com/

Outside the USA—Contact Apple for support and service by phone

See a list of Apple phone numbers around the world.

Contact Apple for support and service - Apple Support 

Watercolor123 wrote:

Most up to date Ventura on IMAC. I cannot send messages reliably. I have tires my normal IMAC MAIL account, and I added a brand new GMAIL account to the IMAC mail accounts. Neither one can send emails that have NO ATTACHMENTS. the imac mail says "sending message" and nothing happens. If i include an attachment, for either IMAC MAIL or the GMAIL account on the mail interface, it is not reliably sent.

From Charter mail web site or GMAIL web site, both work correctly with or without attachments.

I have re booted the computer, the router, the applications, and no progress.

Try turning off the undo send later option and compare your results

turn off scheduling and compare your results...

ref

Send an email in Mail on Mac - Apple Support