From: worldoff9908@gmail.com   
      
   DICK HOFFMAN wrote:   
   > On 9/25/2025 11:20 AM, DICK HOFFMAN wrote:   
   >> On 9/17/2025 2:53 PM, DICK HOFFMAN wrote:   
   >>> On 9/3/2025 7:37 PM, DICK HOFFMAN wrote:   
      
   >> I found something from Gmail that sent me back to to the SECURITY   
   >> settings and there I changed the AUTHENTICATION METHOD to STARTTLS.   
   >> That allowed me to resend four rejected messages so may be the answer   
   >> to my problem. Since the problem seemed to be happening randomly I   
   >> need to watch it for awhile before declaring it fixed.   
   >> Dick   
   >>   
   > No luck, the problem cropped up again for an email reply to my brother.   
   > I marked it as a new message, put an explanation that gmail had rejected   
   > it at the top and resent it and it seems to have gone through to him.   
   > Dick   
      
   I'm kind of confused at the sequence of events.  The way I read your   
   descriptions is that you're submitting through Hotmail, and Gmail is   
   rejecting the message.  If that's the case, what's going on should be   
   something happening between Google and Microsoft, and shouldn't have any   
   bearing on how you have your mail client configured.   
      
   However, it does seem that you may have your Hotmail account   
   misconfigured for SMTP. Microsoft's preference for all mail server   
   connections (and most other authenticated connections to their servers)   
   is MFA that is driven by OAuth2 tokens. Although it may be possible to   
   send from Hotmail without having an OAuth2 token present, that's very   
   much the expectation that Microsoft has.   
      
   It might be that if you don't have OAuth2 set up correctly, it's correct   
   enough that you can send outbound mail through Hotmail, but in a way   
   that's causing Microsoft not to write all the appropriate headers to the   
   message, and where Gmail's handling is based on not seeing what is   
   expected. DKIM is a methodology that has a mail server putting a   
   signature on a message, to communicate to a receiving server that the   
   sender is properly authenticated and is permitted to send mail through   
   that server.   
      
   For outbound (SMTP) settings on a Microsoft-hosted server, the things   
   that need to be defined correctly are as follows:   
      
   - Server name (I forget the one that is used by Hotmail)   
   - Port: 587   
   - Connection Security: STARTTLS   
   - Authentication method: OAuth2   
   - User name: [your hotmail address]   
      
   I have seen it happen occasionally when it seems that a saved OAuth2   
   token gets corrupted. The way around this is to go into the Password   
   Manager, and delete any OAuth2 entries that are associated with your   
   Hotmail account and let it be recreated.   
      
   When you re-create, the first time you connect to the server, you'll get   
   a pop-up with Microsoft branding that asks for your password. When you   
   enter that correctly, and the server authenticates, then a new token   
   will be created in your Seamonkey password store, and you shouldn't have   
   errors submitting mail.  And if Hotmail is correctly accepting, then   
   mail that gets sent to Gmail should have the proper DKIM header.   
      
   Before you start tinkering, I suggest also that you find Hotmail's   
   description of how to set up your connection. They won't give you   
   anything specifically for Seamonkey, but the instructions for   
   Thunderbird should be adequate. However, ignore the directions of how   
   use the Setup Wizard, and look for the guidelines for custom settings.   
   The information you see there should match what I noted above, including   
   the correct server names to be using (both IMAP and SMTP).   
      
   Smith   
      
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