Microsoft requires OAuth2 authentication, not 'Normal Password'. Check the account settings for your account. See https://support.mozilla.org/en-US/kb/microsoft-oauth-authentication-and-thunderbird-202

I have spent a couple of long sessions trying to get things to work. I am 78 and my e-mail is neither related to work or education. I continue to receive Outlook mail via Thunderbird. When I try to send an Outlook e-mail, I receive the message "Login to server smtp-mail.outlook.com with username [edited]@outlook.com failed." "Retry" just returns to the "failed" message. Selecting "Enter New Password" does not provide an opportunity to enter anything but after a short while just returns to the "failed" message. I am able to access the MS account security system. All this from a Windows10 PC - I do have an old 2027 Samsung Android but find it far too fiddly. Sorry to be a nuisance.

Please post your Troubleshooting Information. At the top right of the Thunderbird window, click the menu button ≡, then select Help > Troubleshooting Information. Press the "Copy text to clipboard button" and paste the information into your reply.

Reply had 10220 char - have edited

   Version: 140.10.1esr
   Build ID: 20260429161633
   
   Update Channel: esr
   User Agent: Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:140.0) Gecko/20100101 Thunderbird/140.10.1
   OS: Windows_NT 10.0 19045
  
   Launcher Process: Enabled
   Multiprocess Windows: 0/0
   Fission Windows: 0/0
             Enabled by default
   Remote Processes: 4
   Enterprise Policies: Inactive
   Google Location Service Key: Missing
   Google Safebrowsing Key: Missing
   Mozilla Location Service Key: Missing
   Safe Mode: false
   Memory Size (RAM): 16.0 GB
 
 Mail and News Accounts
   1:
    OUTGOING: , smtp.ic24.net:587, plain, passwordCleartext, true

   4: 
     OUTGOING: , smtp.talktalk.net:587, alwaysSTARTTLS, passwordCleartext, true

   5:      
     OUTGOING: , smtp.gmail.com:465, SSL, OAuth2, true

   account8:
     INCOMING: account8, , (imap) outlook.office365.com:993, SSL, OAuth2
     OUTGOING: , smtp-mail.outlook.com:587, alwaysSTARTTLS, OAuth2, true

 Libraries

     Library
     Status
     Expected minimum version
     Version in use
     Path

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       OK
       0.17.1
       0.17.1.MZLA.140.10.1esr.botan
       C:\Program Files\Mozilla Thunderbird\rnp.dll

       OTR
       Failed to load. OTR chat encryption will not work.
       -
       -
       -

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 Crash Reports for the Last 3 Days

 Remote Processes

   Type: Count

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     Isolated Web Content: 1
     RDD: 1
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 Add-ons

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     Enabled
     Location
     ID

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       *cloud - FileLink for Nextcloud and ownCloud
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       Chambers (UK)
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 Security Software

   Type: Name

     Antivirus: AVG Antivirus
     Antispyware:
     Firewall: AVG Antivirus

 Legacy User Stylesheets

   Active: false
   Stylesheets: No stylesheets found

 Graphics

     Features
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     WebGL 1 Driver Renderer: Google Inc. (NVIDIA) -- ANGLE (NVIDIA, NVIDIA GeForce GTX 1650 Direct3D11 vs_5_0 ps_5_0, D3D11-32.0.15.6094)
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     WebGL 1 Extensions: ANGLE_instanced_arrays EXT_blend_minmax EXT_color_buffer_half_float EXT_float_blend EXT_frag_depth EXT_shader_texture_lod EXT_sRGB EXT_texture_compression_bptc EXT_texture_compression_rgtc EXT_texture_fi

account8: OUTGOING: , smtp-mail.outlook.com:587, alwaysSTARTTLS, OAuth2, true

At the top right of the Thunderbird window, click the menu button ≡ > Account Settings In the left pane scroll down to 'Outgoing Server (SMTP)'. Select the SMTP server for your Outlook account. Change the server name to smtp.office365.com.

I now have the error message: Login to server smtp.office365.com with username alan-rhodes@outlook.com failed. Retry doesn't work and the "Enter New Password" doesn't give any opportunity to do so.

Please post again your Troubleshooting Information. Just the 'Mail and News Accounts' section will do.

Mail and News Accounts ID Incoming server Outgoing servers Name Connection security Authentication method Name Connection security Authentication method Default? account1 (imap) mail.ic24.net:143 None Normal password smtp.ic24.net:587 None Normal password true account2 (none) Local Folders None Normal password account4 (imap) imap.talktalk.net:143 STARTTLS Normal password smtp.talktalk.net:587 STARTTLS Normal password true account5 (imap) imap.gmail.com:993 SSL/TLS OAuth2 smtp.gmail.com:465 SSL/TLS OAuth2 true account8 (imap) outlook.office365.com:993 SSL/TLS OAuth2 smtp.office365.com:587 STARTTLS OAuth2 true Libraries

Ok, this looks good now. You can try to delete the password/OAuth token Thunderbird has remembered for the Outlook account. This will trigger a re-authentication for the account.

At the top right of the Thunderbird window, click the menu button ≡ > Settings > Privacy & Security > Passwords > Saved Passwords Remove any password/OAuth token related to the Outlook account.

For the re-authentication to work properly you need to allow cookies in Thunderbird. https://support.mozilla.org/en-US/kb/microsoft-oauth-authentication-and-thunderbird-202#w_changes-or-problems-you-may-encounter

Initially, this didn't seem to work. However, I had noticed that my old TalkTalk e-mail was the "Primary Alias" on my Microsoft account. Changing to the Outlook e-mail as the primary might have been the clincher. Thunderbird is now happily both receiving and sending Outlook e-mail.

Thanks for all your help. Alan