[ANSWERED]Sending to Gmail

Hi All.

My Gail stopped working. it worked for months.
The account is not locked.

Email sending Settings:
smtp.gmail.com
SMTP server port - 465 (tried 587) Use SSL is checked
user name: is full email address
Password (it is correct)
Reply to: same full email address

This is the message

email sending - done sleeping
Debug <<-- start smtp connection -->>
Debug email sending - openning connection...
Debug email sending - connection established1
Debug email sending - no response from server
Debug email sending - starting SSL...
Debug SENT: GetImInfo packet to see if connection is alive
Debug email sending - connection established2
Debug email sending - SSL handshaking completed
Debug email sending - authen mechanisms: (
LOGIN,
PLAIN,
XOAUTH,
XOAUTH2,
"PLAIN-CLIENTTOKEN",
OAUTHBEARER
)
Debug email sending - authenticating rjrossxx@gmail.com using authen LOGIN
Debug email sending - authenticating rjrossxx@gmail.com using authen PLAIN
Debug email sending - authenticating rjrossxx@gmail.com using authen XOAUTH
Debug email sending - authenticating rjrossxx@gmail.com using authen XOAUTH2
Debug email sending - authenticating rjrossxx@gmail.com using authen PLAIN-CLIENTTOKEN
Debug email sending - authenticating rjrossxx@gmail.com using authen OAUTHBEARER
Debug email sending - authentication failed
Error email send authentication failed
Debug email sending - connection closed
Debug email sending - completed
Debug <<-- end smtp connection -->>
Error email re-send scheduled in 10 minutes
Debug email sending - sleeping before retry

What am I doing wrong?
Bob Ross

Try to login on the web. See if that works. Sometimes gmail yahoo hotmail identify this kind of email traffic as spam. I had the same problem had to switch to hotmail. But there it happens every 10 days. I then need to login manually then it works again.


Sent from my iPhone using Tapatalk

Gmail web mail from the computer running Indigo works just fine no problem logging in and sending something

Bob

I have the same issue. I used iCloud mail for years successfully. Trying Gmail and I also fail to get outbound emails sent anymore. No issues with either account otherwise (e.g., I can send, receive, etc., as expected.)

Well, I think I figured it out.

On the mac in systems preferences is "Internet Accounts". I you try and set it up it returns an error. That I need an "Application Specific Password". That got me thinking.

I Goggled that and got to here:

https://support.google.com/mail/answer/1173270?hl=en

Well, I created one, pasted it onto the password field in Indigo . IT WORKED

I did not need to add it to the "Internet Accounts" just use that new Google generated password.

The strange world of the internet!

Bob

Bingo! Same issue for my iCloud password. I forgot that application specific passwords had become the requirement. There you go! Thanks for solving the mystery!

[matt (support)]

Good info. Thanks for posting the solution.