SMTP configuration - Must issue a STARTTLS ?

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DrZappo
Posts: 1
Joined: Sun Mar 27, 2011 9:11 pm

SMTP configuration - Must issue a STARTTLS ?

Post by DrZappo »

Need some help setting up the email fuction. It appears the SMTP Authentication is failing with "Must issue a STARTTLS". I see no hits here (HELP!)... Current setting are:

SMTP Server: smtp.gmail.com
Port: 587 (used 465 as well - same results)
with 'SMTP Authentication' checked
vaild login/password is provided

-------

Results below is provided during the "test":

SMTP Connecting.
<220 mx.google.com ESMTP g69sm1697131yhc.88
>EHLO Zappo-NB
<250-mx.google.com at your service, [97.96.74.248]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
SMTP Send mail.
>MAIL FROM:<drxtz@gmail.com>
<530 5.7.0 Must issue a STARTTLS command first. g69sm1697131yhc.88
SMTP Send mail Failed.
>QUIT
<221 2.0.0 closing connection g69sm1697131yhc.88
SMTP Close.
RiseFly
Site Admin
Posts: 1077
Joined: Tue Nov 03, 2009 2:51 pm

Re: SMTP configuration - Must issue a STARTTLS ?

Post by RiseFly »

Sorry, BestSync does not SSL/TLS authentication when using SMTP now.
Please use an e-mail account that need not SSL/TLS authentication.
Sandeep
Posts: 9
Joined: Mon Oct 29, 2012 5:30 am

Re: SMTP configuration - Must issue a STARTTLS ?

Post by Sandeep »

Does bestSync support this feature now? I tried to send email to distribution list and this also has failed. I receive email when I add my email ID to recipient list but when I add a DL in which my mail id is also include I do not receive emails.
RiseFly
Site Admin
Posts: 1077
Joined: Tue Nov 03, 2009 2:51 pm

Re: SMTP configuration - Must issue a STARTTLS ?

Post by RiseFly »

BestSync supports SSL/TLS now.
The steps to use SSL/TLS when send email:
1. Click "Option"/"Option" menu.
2. Click "Email" tab in the "General Option" dialog box.
3. Check "This server requires an encrypted connection(SSL)" option in the "Email" tab.
4. Please set the "SMTP Port" that server allows SSL/TLS connection (according to the server's setting).
Sandeep
Posts: 9
Joined: Mon Oct 29, 2012 5:30 am

Re: SMTP configuration - Must issue a STARTTLS ?

Post by Sandeep »

The exchange server which are using has only TLS port.
When I send a test email with option "This server requires an encrypted connection(SSL)" checked, I get below error:

"SMTP Connecting.
Connect to server by SSL.
winsock:GetHostByAddr:error:(0x00002afc):The requested name is valid, but no data of the requested type was found.
SSL:ClientHandshakeLoop::InitializeSecurityContext.(0x80090308):The token supplied to the function is invalid
SSL:Connect Failed.
Failed to connect to the SMTP server."

When I send a test email with option "This server requires an encrypted connection(SSL)" unchecked, I get below error:

"SMTP Connecting.
<220 PN1PR01CA0002.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 20 Nov 2015 05:33:18 +0000
>EHLO my_machine_name
<250-PN1PR01CA0002.outlook.office365.com Hello [*********IP]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250 CHUNKING
SMTP Send mail.
>MAIL FROM:<my_mail_id>
<530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
SMTP Send mail Failed.
>QUIT
SMTP Close."

We have tested the SMTP configuration with a code. That works for us when we set SSL to false and TLS to true.

Can BestSync be configured to use above parameter values?
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