Sent messages sit in the outbox. No error messages. Sent messages from other devices now appear on the iMac which I don't believe they did prior.
Server settings, account info all look ok.
Any help appreciated.
iMac 21.5″, macOS 10.15
Gulp, sounds scary...
Safe Boot, (holding Shift key down at startup), does the problem occur in Safe Mode?
Safe mode attempts to repair Disks & clears lots of caches & loads safe Drivers, & prevents loading of 3rd party extensions, so if Safe Mode works try again in regular boot.
Hi jmwlmsn,
In that case, we would recommend reviewing this article: If you can’t send emails in Mail on Mac.
Thanks again!
Are you running any VPN, Anti-Virus, or Cleaning apps?
In a Browser login to your WebMail, does that work OK?
Merci — did all those things— iphone and iPad outgoing mail died along the way but now everything seems to work. Weirdly incorrect error messages. Like sender email address invalid. Apple ID verification code wouldn’t take. After all my messages finally sent from outbox, new messages suddenly blocked again. All settings had reverted to crazy ones. User name and password should not say OPTIONAL in SMPT section I don’t think.
thanks again.
Started in safe mode. Mail still sitting in outbox. Redid all mail server settings. (Password authentication bounces to “off" a lot.) Finally got an email to send. Restarted in regular mode, now it's back to mail sitting in Outbox.
Went to Keychain Access and deleted more mail-related passwords I thought I had taken care of yesterday. The three old “com.apple.account.SMTP.password….", etc. with my ISP in there I deleted as well and now can’t mail from anywhere but webmail. Obvious mistake. Error message says "SSL error has occurred and secure connection can’t be made."
Accounts screen says “Unable to verify account name or password.” Odd because I can log into my ISP account for webmail and my iPad and Iphone receive email. iCloud account says it’s offline and I can’t figure out how to get that back online. I’ve logged into iCloud numerous times. Also can’t find the screen with SSL option to check.
I’ll restart in safe mode again…...
Outgoing mail blocked from my 2017 iMac with Catalina iOS. (Mail only sends from my mobile devices fine.)
No extras—cleaned all that old antivirus stuff out previously.
Yes, on web mail account, all works fine.
Will do. Looking to solve slow Mac problems so this may help that as well. Thx.
Did it help?
Seems ICloud account was in the way somehow. Now iMac mail is working. Thanks! Think it was all that keychain access business getting straightened out.
Hi jmwlmsn,
We understand you are unable to send emails from your iPhone or iPad.
We would recommend reviewing this article: If you can’t send email on your iPhone, iPad, or iPod touch.
Hope this helps!
Thank you for using Apple Support Communities.
Cheers!
Have you changed your eMail password lately?
Works sometimes even if you haven’t
Open Keychain Access in Utilities, then either check the Password under that item, change it, or delete it and start over.
Enter the part after the @sign in the search bar.
You may have duplicate or more entries in Keychain Access.
If using a browser to login via WebMail works it's not Name or Password, but likely old passwords interfering.
There''ll be at least 2 entries, maybe more.
The trouble is that Mac Mail almost always chooses the old Passwords if you don't change or get rid of the old ones.
Restart to clear some caches.
The big bugaboo with Mail is finding the keychain for any auto setup Mail accounts, if IMAP it usually involves deleting the account & setting it up again to fix it.
Great to hear I could help, take care mu friend! :)
Thanks, you too!
Outgoing mail is blocked on my iMac but not on iPhone or iPad. Any help appreciated.
