problem with sending mail with Catalina

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Level 1

4 points

problem with sending mail with Catalina

Since upgrading to Catalina on Mac Powerbook 2012 I can't get mail to send reliably (and message just sits in Outbox). Receives OK, but typically requires Quit and reopen mail to send. Does this with mail accounts from all email accounts (gmail, iCloud etc). Have spent over 8 hours with apple support doing everything from deleting and adding mailboxes, trying to add server info manually, reinstalled Catalina two days ago, etc. I have another Powerbook (1 year older) running High Sierra and everything works perfect. Mail work perfect on iPhones as well. Last agent basically said there is nothing more they have to try and it appears Catalina mail seems to have an issue and I need to upgrade OS (which I can't do on this machine). Surely I am not the only person trying to use Apple mail app with Catalina 10.15.7? Anyone else running such successfully? Anyone else having similar issue or had the issue but resolved it? Please, please help.

Posted on Oct 22, 2021 2:32 PM

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Answer 1

PRP_53

Level 10

84,505 points

Oct 24, 2021 4:24 AM in response to BCJJ

Are the e-mail accounts using POP to IMAP ?

Specific to Google e-mail issues If Mail on your Mac keeps asking for your password

Your email provider needs you to update or reset your password for security reasons. For example, if you're using Google’s two-step verification, your Gmail account in Mail requires the appropriate app-specific password.

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Answer 2

PRP_53

Level 10

84,505 points

Oct 23, 2021 2:31 AM in response to BCJJ

Are there any Third Party Applications that will interfere with the normal operation of the OS, alter, modify, remove or delete or attempt to do so is an invitation for disaster and may require a Reinstallation of the OS.

This includes AntiVirus, Cleaners, Optimizes, UnInstaller etc.

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Answer 3

BCJJ Author

Level 1

4 points

Oct 23, 2021 9:12 PM in response to PRP_53

Don't believe so, none of the four you mentioned, and no vpn. I notice that when I do a Mail, Preferences the Account information tab seems to populate correctly for the account or accounts I set up (using the add account +, Gmail, un and pw etc), and the Mailbox Behaviour seems fine, however the Server Settings is a bit of a mystery. It has "none" and the account(s) in the pull down, but regardless which one I check and then click 'Edit SMTP Server Settings', the window shows up empty with no accounts in the main box, and no info below, and I can not manually add info below (name, em, pw, SMTP server, Port etc) unless I add another one. If I add one with all the correct info the list shows the auto one and the one I created, only the one I created is editable, and it doesn't work any better. So basically after about 40 hours of fighting with it my (novice) diagnosis is that the Catalina OS has issues with communication (i.e.authentication and holding a connection) with the SMTP Server. Also I cannot get a response from Gmail when I try to add the account manually (other/mail) in setup, which is also weird because before we reinstalled Catalina a few days ago I could add manually (although it would conflict with some auto set up one and not work). Anyone else out there using Catalina and Mail can give any hints please...?

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Answer 4

BCJJ Author

Level 1

4 points

Oct 24, 2021 12:02 PM in response to PRP_53

No Pop, just IMAP. Doesn't ask for password. Just has the losing connection to SMTP issue for all emails we try (Telus.net, gmail, imail)

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problem with sending mail with Catalina

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