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Outlook SMTP, Sent messages never leave the outbox...
 
#1
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I'm running Home v12.2. I've added two outlook accounts: IMAP works perfectly, SMTP does not. All messages I send just sit in the outbox. Initially the software asks me to re-insert my password (despite the setup including my password) and then returns the 'Client not authenticated to send mail' error.
The accounts are set up correctly. I can find no answer in these forums and have had no response from support. Does anybody have any thoughts?

FYI I have various Gmail accounts, all of which work perfectly well with TB; the outlook accounts all work as they should using the Outlook software at work and Fairemail on my mobile.
 
 
 
#2
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Have you tried OAuth 2.0 for authentication?
I volunteer as a moderator to help keep the forum tidy. I do not work for Ritlabs SRL.
 
 
 
#3
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I have no authentication options only one tickbox to 'perform SMTP authentication (RFFC 2554)'
 
 
 
#4
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Quote
Stephen Hocker wrote:
I have no authentication options only one tickbox to 'perform SMTP authentication (RFFC 2554)'

Check out "Authentication..." under "Receive mail", more options should be there.
 
 
 
#5
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I'm using oauth for the imap inbound connection. There is no oauth2 option.  
 
 
 
#6
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Stephen Hocker wrote:
I'm using oauth for the imap inbound connection. There is no oauth2 option.

That is actually OAUTH2, it's fine.

Two things to try come to mind:
1. Switching between STARTTLS and TLS in TB account properties.
2. Forcing re-authentication. I wouldn't know how to exactly do that with Outlook, but with GMail it would involve going to Google account properties, finding the list of apps with permissions, and deleting TB from there. I assume something like that may exist for MS accounts.
 
 
 
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