Weird Upgrade Problem to 7.11.18 - emails

Ok so I’ve got a clean 7.11.18 installed and email works fine.

My upgraded version (that has all my data!) the email stopped working “SMTP Could not Authenticate”

When I change my credentials and “test” it sends. After I save my credentials it no longer works and can’t authenticate.

So…

I tried using my vanilla install (that works) and connected it to the production database to see if email works. It doesn’t. So that narrows it down to the DB and not any of the files or configuration.

I checked in the db and it is saving the encrypted password. I’m totally stumped. Anyone have any other ideas I can try?

Can you check if it saving the correct encrypted password, by comparing to the encrypted value on the previous server that works?

After that, go for extra logging:

I tried that. The values are different between the working DB and the non working DB (in terms of password). I tried changing the DB value in the non-working DB to the working value. That didn’t work either. Failed to authenticate.

@pgr I tried that, there’s nothing new in the logs. Just cannot authenticate. Here’s what shows in the SMTP log. I doesn’t seem to be super helpful either.

3: Connection: opening to ssl://smtp.sendgrid.net:465, timeout=300, options=array()
3: Connection: opened
2: SERVER -> CLIENT: 220 SG ESMTP service ready at geopod-ismtpd-3-0

1: CLIENT -> SERVER: EHLO XXXXXXXXXXXXX.com (removed for privacy)

2: SERVER -> CLIENT: 250-smtp.sendgrid.net
250-8BITMIME
250-PIPELINING
250-SIZE 31457280
250-AUTH PLAIN LOGIN
250 AUTH=PLAIN LOGIN

1: CLIENT -> SERVER: AUTH LOGIN

2: SERVER -> CLIENT: 334 VXNlcm5hbWU6

1: CLIENT -> SERVER: —obfuscated—
2: SERVER -> CLIENT: 334 UGFzc3dvcmQ6

1: CLIENT -> SERVER: —obfuscated—
2: SERVER -> CLIENT: 451 Authentication failed: Could not authenticate

1: SMTP ERROR: Password command failed: 451 Authentication failed: Could not authenticate

3: SMTP Error: Could not authenticate.
1: CLIENT -> SERVER: QUIT

2: SERVER -> CLIENT:
1: SMTP ERROR: QUIT command failed:
3: Connection: closed
3: SMTP Error: Could not authenticate.

It clearly says password command failed. However, when I “test” it works when I save the exact password, fails authentication. Just don’t get it?

WOW!!! solved it. Thanks @pgr for your help. I spent all day on this problem and wasn’t getting anywhere.

For giggles, I restarted my VPS. It now works!!!

Weird, both installations were on the same VPS. I still haven’t figured out what the issue was, but it’s backup and running!

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