Ok. So, the deeper I dug, the more complex the problem became. I decided just to start over fresh and reinstalled sbbs. The problems I had before are gone except for one. I am unable to send email from my server to an outside server. I get this error:

7/31 11:13:45a 2620 SEND/TLS [127.0.0.1] ERROR 'Received TLS alert message: Handshake failure' (-15) setting session active

And the return email I get says:

TZ: fed4
vert.synchro.net reporting delivery failure of message
from Sys64738 to -----------@gmail.com

Reason:
gmail-smtp-in.l.google.com replied with:
"550 5.7.26 https://support.google.com/mail/answer/81126#authentication d9443c01a7336-1fed7f9e5a3si153261305ad.442 - gsmtp"
instead of the expected reply:
"250 ..."

---
þ Synchronet þ GeoSync - geo.synchro.net

Sys64738 wrote to All <=-

Ok. So, the deeper I dug, the more complex the problem became. I
decided just to start over fresh and reinstalled sbbs. The problems I
had before are gone except for one. I am unable to send email from my server to an outside server. I get this error:

7/31 11:13:45a 2620 SEND/TLS [127.0.0.1] ERROR 'Received TLS alert message: Handshake failure' (-15) setting session active

And the return email I get says:

TZ: fed4
vert.synchro.net reporting delivery failure of message
from Sys64738 to -----------@gmail.com

Reason:
gmail-smtp-in.l.google.com replied with:
"550 5.7.26 https://support.google.com/mail/answer/81126#authentication d9443c01a7336-1fed7f9e5a3si153261305ad.442 - gsmtp"
instead of the expected reply:
"250 ..."

Maybe this is the problem:

https://support.google.com/accounts/answer/185833?hl=en



... So easy, a child could do it. Child sold separately.
--- MultiMail/Linux v0.52
þ Synchronet þ Palantir BBS * palantirbbs.ddns.net * Pensacola, FL

Maybe this is the problem:

https://support.google.com/accounts/answer/185833?hl=en

Thanks for the reply, but I don't see where having an app password would help in this situation. Or may be I'm missing the point?

---
þ Synchronet þ GeoSync - geo.synchro.net

SYS64738 wrote to Gamgee <=-

Maybe this is the problem:

https://support.google.com/accounts/answer/185833?hl=en

Thanks for the reply, but I don't see where having an app password
would help in this situation. Or may be I'm missing the point?

Yeah, I think I had this backwards... You might need such a thing when attempting to send email *from* a gmail account, such as something
automated like a cron job or similar. I now remember that you're
trying to send *to* a gmail account.

Hope you get it figured out.


... Gone crazy, be back later, please leave message.
=== MultiMail/Linux v0.52
--- SBBSecho 3.20-Linux
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þ Synchronet þ Vertrauen þ Home of Synchronet þ [vert/cvs/bbs].synchro.net

Yeah, I think I had this backwards... You might need such a thing when attempting to send email *from* a gmail account, such as something
automated like a cron job or similar. I now remember that you're
trying to send *to* a gmail account.

Hope you get it figured out.

Thanks. I appreciate your trying to help.

---
þ Synchronet þ GeoSync - geo.synchro.net