External SMTP Changes and changelog for Gmail

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Ronald Nissley

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Jan 30, 2012, 1:17:15 PM1/30/12
to Gmail-Users
The average Gmail user may not be aware of this, but for a while,
Gmail included functionality that essentially allows it to act as a
"cloud" replacement of the desktop MUA (Thunderbird, Outlook, etc.).
You could download e-mail via POP from an external mail server and
relay e-mail via authenticated SMTP through an external server.
Now, however, when I add an external "send mail as" account, I don't
see an option to specify an external SMTP relay or credentials to
authenticate to an external relay. There is a new "treat as an alias"
option I don't want and e-mail sent from an external account now shows
return-path and other Google-related header information that was not
present with the previous external relay setup. Is the authenticated
external relay option gone altogether or have the settings relocated?
Is there a changelog for Gmail? It would be nice if a dated detailed
changelog would be published, so Gmail users could see at a glance
changes that have been introduced.

Thank you,

Ron

Zack (Doc)

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Jan 31, 2012, 7:24:39 AM1/31/12
to gmail...@googlegroups.com
Ron,

The Official GMail Blog has a "What's New" link which lists changes, but it's not clearly dated, nor completely thorough.  It's all we've got to go on.

One reason for this, I think, is because you and I may not be running the same version anyway.  GMail has always rolled changes out to it's users rather than deploying to all at once.  Some changes get rolled back and never make it to everyone, and there might be several "test" versions out there with us users at any given time.

All that said... 2 months ago I added a new from address (actually I collected mail into the account through POP and set up the send at the same time) and was able to set it up with authenticated relay.  I just verified that they are still set up that way, but did not try setting up another.  I would guess that if you don't select "treat as an alias" it might offer the options then.  As I recall, it might not have asked for authentication until it verified it could reach the relay and it asked for credentials.

Zack


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Ronald Nissley

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Jan 31, 2012, 10:03:02 AM1/31/12
to Gmail-Users
> e-mail sent from an external account now shows return-path and
> other Google-related header information that was not present with
> the previous external relay setup.

To be more precise, such e-mail doesn't appear to be sent through an
external relay at all, but instead, relayed by Google's servers. In my
opinion, characteristics of e-mail sent this way are more spam-like.

Ronald Nissley

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Jan 31, 2012, 9:52:17 AM1/31/12
to Gmail-Users
> The Official GMail Blog has a "What's New" link which lists changes, but
> it's not clearly dated, nor completely thorough.  It's all we've got to go
> on.
>
> One reason for this, I think, is because you and I may not be running the
> same version anyway.  GMail has always rolled changes out to it's users
> rather than deploying to all at once.  Some changes get rolled back and
> never make it to everyone, and there might be several "test" versions out
> there with us users at any given time.

My question about a detailed changelog was more a suggestion than a
question. :-) Along with an "About Gmail" that shows a version/
revision number, it would help users understand why "their" Gmail
works as it does (or doesn't).

> All that said... 2 months ago I added a new from address (actually I
> collected mail into the account through POP and set up the send at the same
> time) and was able to set it up with authenticated relay.

That's exactly how I was trying to add an external sending account
(first adding a POP account and choosing the option to also send
through that account) when I stumbled on what appears to be new
(reduced) functionality.

> I would guess that if you don't select "treat as an alias" it might offer
> the options then.  As I recall, it might not have asked for
> authentication until it verified it could reach the relay and it asked for
> credentials.

I unchecked the option to "treat as an alias" as this feature is
certainly not what I'm looking for:
http://support.google.com/mail/bin/answer.py?hl=en&answer=1710338&ctx=gmail
Adding the POP account was successful, and the external address
verification (for sending) was successful, but it never gave me an
opportunity to enter the hostname (fqdn), credentials and port/
encryption settings for an external relay.
I have successfully used this feature several times in the recent
past, so I'm guessing that this apparent feature reduction is part of
Gmail's "new look".

Thank you,

Ron

Ronald Nissley

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Jan 31, 2012, 12:37:47 PM1/31/12
to Gmail-Users
Additional info: for wholly external accounts, the option is still
available to authenticate/send through an external relay. What is no
longer working is to treat other Gmail (personal or Google Apps-based)
accounts as altogether external. When detected that such an account is
being added, the option to set an external relay hostname and
credentials is not offered. If you send e-mail "from" a Google Mail
account added that way, headers reveal the e-mail address of the
account to which you added the "external" account, in Return-Path and
other fields.
In my case, I was trying to add an account in a domain that is also in
a limited Google Apps pilot test (MX records for this domain only
include my servers, so mail for this domain doesn't route through
Google). When adding the information for the POP account, I used a
completely external relay (that I manage): hostname of my server, and
credentials for my external account (usernames even differ; Google
requires the full e-mail address, my server requires/allows only the
first part of the e-mail address). Still, when adding another account
for sending, it apparently detects that the e-mail address is also
hosted in Gmail.
I was hoping to manage e-mail in two domains from a single Gmail login
and present distinct domains/accounts to recipients (why I didn't use
a domain alias in the first place). So it seems the only workaround is
to use separate logins and the multiple sign in feature (or multiple
browsers) or setup multiple accounts in a traditional MUA.
Google: is this a case of feature attrition based on some usage stats?

Zack (Doc)

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Feb 1, 2012, 1:51:56 AM2/1/12
to gmail...@googlegroups.com
Very odd, since the account I was recently configured that is working as you want, is a Google Apps account.  And I was on the new look when I did it, but the Apps account was still on the old look.  Maybe that's the corelation?!?

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