Topic: smtp.gmail.com issues (resolved)

[NomadOfNorad]

A month ago, my ISP decided to switch from using their own in-house email system to using gmail for all incoming and outgoing mails.  I am only just now getting around to changing my SME server settings to accommodate.

Most of my mail comes in by way of pop server accounts at my webspace provider, but I have one mailbox at my ISP that I also retrieve mails from into a box at my SME server.  I can't seem to get that to work, either, but first things first.

I went to server-manager > Configuration > E-mail and under SMTP Server set:

smtp.gmail.com:587
SMTP enabled
(myusername@ISPdomainname)
(myexistingpassword)

I try sending out a test mail, and immediately I get back a bounce message:

Hi. This is the qmail-send program at [myowndomainname].com.
I'm afraid I wasn't able to deliver your message to the following addresses.
This is a permanent error; I've given up. Sorry it didn't work out.

<*****@****.com>:
Connected to 127.0.0.1 but sender was rejected.
Remote host said: 530 5.7.0 Must issue a STARTTLS command first. d29sm9869792and.12

It doesn't seem to matter if I've got the :587 added to the end of the SMTP server field or not, the error is the same.  I'm assuming I'm going to have to get down under the hood somewhere and fiddle with something, but I'm not a *nix techie.

I have looked at the thread over here, which is talking about the same issue, but no one seems to have answered the actual, original question and instead have only focused on the retrieving-mails-from-gmail issue.  In any event, I followed the instructions over here, which gave me the option to select secure SSL in retrieving my mails for that box, but I still haven't seen the mails show up in the appropriate box.  (Mails for everything else are coming in fine but, remember, that's from a different provider.)

Have anyone else been able to get outgoing mails to work through gmail with SME server?

edit:

And for clarification, my ISP have instructed, in their online docs:

7. Set the Server Name: to smtp.gmail.com. Set the Port: to 587. Select Use name and password and enter your full Clearwire email address in lower case (including '@clearwire.net') in the User Name: field. Select TLS from the Use secure connection radio buttons and click OK.

...so part of the issue is they require TLS for this to work.

[CharlieBrady]

I went to server-manager > Configuration > E-mail and under SMTP Server set:

smtp.gmail.com:587
SMTP enabled
(myusername@ISPdomainname)
(myexistingpassword)

I try sending out a test mail, and immediately I get back a bounce message:

Hi. This is the qmail-send program at [myowndomainname].com.
I'm afraid I wasn't able to deliver your message to the following addresses.
This is a permanent error; I've given up. Sorry it didn't work out.

<*****@****.com>:
Connected to 127.0.0.1 but sender was rejected.
Remote host said: 530 5.7.0 Must issue a STARTTLS command first. d29sm9869792and.12

What happens if you use port 465? SME server doesn't support STARTTLS for outgoing SMTP.

[NomadOfNorad]

What happens if you use port 465? SME server doesn't support STARTTLS for outgoing SMTP.

Well, I've switched to that port, and have just now sent a test message to my yahoo.com box.  I didn't get the instant bounce this time.  On the other hand, the mail hasn't shown up at yahoo yet, either. 

[NomadOfNorad]

Well, I finally called the ISP and discussed the problems with them.  I wasn't able to get the outgoing mail problem fixed, and it seems to be a problem with SME Server here not dealing with TLS issues right.  I solved the outgoing mail problem by switching to my webspace provider's SMTP service.  (And that took a lot of fiddling around, too...  so far as I can tell, the problem there seemed to be with my complex passwords, and going to a simpler password fixed it... grrr...)

As for the problem of not being able to collect my mails from the POP server... it turns out there was some sort of issue with the passwords not having transitioned over to the new gmail.com-based system, and they had me reset and re-enter the (same) password into the mailbox account via their web front-end.  They stated that that was a very rare issue, though.  Anyway, I did that with the pop mail box, and did the same with a second pop mail box there, and it enabled me to get the mails off the pop box and into the SME server's box for that account.  The password issue had also caused me to be unable to access the box on their service via their own web-based front end, too.

Anyway, everything's fine n#$^($^&(%^&(
NO CARRIER

[CharlieBrady]

Well, I've switched to that port, and have just now sent a test message to my yahoo.com box.  I didn't get the instant bounce this time.  On the other hand, the mail hasn't shown up at yahoo yet, either. 

So what do your qmail logs say about the progress of that message. There are three possibilities - it is still on your server waiting to be sent, it has been rejected by your ISP's server, or it has been accepted by your ISP's server.

[CharlieBrady]

Well, I've switched to that port, and have just now sent a test message to my yahoo.com box.  I didn't get the instant bounce this time.  On the other hand, the mail hasn't shown up at yahoo yet, either. 

Has it shown up yet?

[I've noticed that most mail is very slow to be accepted by yahoo's mail servers.]