Since my ISP reorganised, I haven't been able to send mail from Pegasus. The details:
18:48:31.635: --- 29 Mar 2026, 18:48:31.635 ---
18:48:31.635: Connect to 'smtp.gmail.com', timeout 300 seconds, flags 16842753.
18:48:33.757: >> 220 smtp.gmail.com ESMTP 5a478bee46e88-2c3c6e9d38fsm6941624eec.23 - gsmtp
18:48:33.758: << EHLO [192.168.1.7]
18:48:33.894: >> 250-smtp.gmail.com at your service, [74.116.44.159]
18:48:33.894: >> 250-SIZE 35882577
18:48:33.894: >> 250-8BITMIME
18:48:33.894: >> 250-STARTTLS
18:48:33.894: >> 250-ENHANCEDSTATUSCODES
18:48:33.894: >> 250-PIPELINING
18:48:33.894: >> 250-CHUNKING
18:48:33.894: >> 250 SMTPUTF8
18:48:33.897: << MAIL FROM:oldhen@velociter.net SIZE=1261
18:48:33.922: >> 530-5.7.0 Must issue a STARTTLS command first. For more information, go to
18:48:33.922: >> 530-5.7.0 https://support.google.com/a/answer/3221692 and review RFC 3207
18:48:33.922: >> 530 5.7.0 specifications. 5a478bee46e88-2c3c6e9d38fsm6941624eec.23 - gsmtp

I went to Google, found 530.5.7.0, and (surprise surprise) Google's answer was "use Gmail."

My ISP -- and my only choice of ISP where I live-- is Velociter.net and their technician got smtp working on my Win11 Surface Pro when I brought it in to the Velociter office, but so far not on the Win10 desktop. Suggestions welcome.

This tells you that you need to select the "via STARTTLS" radio button in the Security tab of the Gmail SMTP definition.

Tools > Internet options > Sending tab > select the Gmail SMTP host > click the Edit button > select the Security tab > tick the "via STARTTLS" radio button.

Couple of questions?

1. Did you setup the gmail using Auth option?If yes, have you changed your gmail password. If so, you have to run the process again, since old setup will no longer be valid.
2. If you are using the gmail app password setup, the same would apply. If you changed the gmail password, the old app password is no longer valid, and has to be recreated.

What version of Pegasus are you running.

Additionally, you have to activate the POP3 and SMTP with you gmail account, default doesn't allow it and expects you to use the web browser.

Couple of questions?

1. Did you setup the gmail using Auth option?If yes, have you changed your gmail password. If so, you have to run the process again, since old setup will no longer be valid.
2. If you are using the gmail app password setup, the same would apply. If you changed the gmail password, the old app password is no longer valid, and has to be recreated.

What version of Pegasus are you running.

Additionally, you have to activate the POP3 and SMTP with you gmail account, default doesn't allow it and expects you to use the web browser.

Same result. This has nothing to do with gmail. I can't send ANY mail from Pmail -- Gmail or my Velociter.net addresses. I think it's somewhere in Win10 or the ISP but decided to check here in case I could solve the problem within Pmail.

However, in answer to the other info you requested in case it might help someone else: using latest version of Pmail (4.91.1746, August 2025)

The only way to set up a Gmail address is with the wizard, which walks one through the OAUTH process. Setting up as formerly 'normal' with password, accountname@..., ports, etc, doesn't work.

According to Google, device passwords have been defunct since 2022, but when setting up an account via the Wizard (only way to set up a new Gmail account to use OAUTH), there's an option, on by default, for Gmail to update the account -- i.e., replace device pw with OAUTH.

No, no changes in account. Mailwasher provides a check as I set all the Gmail and Velociter accounts up using the same info and MW accesses all Gmail and Velociter mail.
Yes, Pop3 & SMTP are activated in all Gmail accounts (has to be done for each account).

Error message when trying to send mail is the same except for date -- no point in repeating it here.

molly

The error states that it is expecting a STARTTLS command. Did you address that?

This may only be relevant to Gmail SMTP since that was the source of the error you posted. Velociter.net may have different requirements.

Also, just observed in the error content is the fact that you used Gmail SMTP to send mail from your velociter.net address. Once upon a time, Gmail would allow this. I don't know if they still do, but most SMTP servers don't. The MAIL FROM: address must belong to the SMTP service being used. This does not have anything to do with the error though.