Email issues with Outlook for Mac

[CharlesP]

Since Friday last week I keep getting this message when I try to send using Outlook for Mac on my MacBook.

"Email could not be sent

The server for account "BT Mail" returned the error "invalid user ID or password from 77.99.191.79." Your username/password or security settings may be incorrect. Would you like to try entering your password again?"

The same settings work perfectly well on Outlook for iOS on both iPhone and iPad.

Logging on to Webmail - allows sending.

I am tearing my hair out and the BT help on thewe website is useless.

HELP, please

[nnapier]

I recently tried out the new Outlook for Mac and found that the 'wizard' for adding email Accounts needed tweaking for BT. (Make sure it doesn't default to POP, and make sure receiving and SMTP server names are both mail.btinternet.com. (It put in an O2 SMTP server for some unknown reason).

I had a similar problem sending, which was solved by making sure SSL was UNCHECKED for the SMTP server, and letting the mac choose Port 25. Everything then worked for me OK.

New Outlook for Mac Issues:

Moving to the new Outlook for Mac has been a nightmare.

I found that BT emails were not being indexed properly in Search in the new Mac Outlook version (gmail and iCloud ones were fine). After spending time rebuilding spotlight indexes, Microsoft profiles, re-installing Office and moving emails at the BT mailbox source I gave up and reverted to the old Mac. Where search works fine.

I have given up on the new Mac Outlook interface - its lacking many features, and the indexing problem makes it unusable.

Not sure any of this helps you, but maybe worth checking your settings.

[CharlesP]

Thank you.

I solved it by trial and error and it was as you noted in your reply.

I agree New Outlook for Mac is not great - lacking many features in the old Outlook - I am thinking of moving back to the old.

[licquorice]

I certainly wouldn't use the insecure port25 for outgoing (SMTP) mail, with SSL selected you need to use port 465

[nnapier]

Glad you found a solution.

Have you found any issues with Searching for emails in the new Outlook for Mac? I was getting incomplete results and it was taking ages making it useless. (Mac OS 10.15.7 - Outlook 16.62).

It was weird as Gmail and iCloud emails were getting indexed OK, and found in search. Just the BT ones missing which makes me wonder whether there is an issues with these 'non-standard' IMAPI accounts and Outlook.

I've found a lot about indexing issues, tried all the suggestions, and it still doesn't work. Any thoughts?

Thanks

[nnapier]

When I use port 465 (and 587 which I saw suggested somewhere) I get an error sending:

"The connection to the server failed or was dropped."

Any thoughts as I agree about port 25.

Thanks

Error Code 3253

[licquorice]

Sorry, no. I'm afraid I have no experience of the arcane workings of Apple devices.

Port 465 with SSL works just fine on Outlook for Windows.

[nnapier]

Thanks,

My mistake here.

With PORT 465 selected AND the SSL Checkbox ticked it worked.