SMTP sending issue

[PhilthyM]

Hi, Gargoyle n00b here...

It appears my password is being blocked somehow when trying to send emails from a Mac. I have tried a few things troubleshooting but just can't figure out where to look next. Any ideas greatly appreciated.

If I connect via my old Untangle box, everything works fine. If I simply swap in the Gargoyle box, email sending is blocked. This is consistent and repeatable, so I guess I have to conclude it is something in Gargoyle that's stopping me.

I have contacted my mail provider and they helpfully pointed me to the Spamhaus blocklist and sure enough there is the advisory:

http://www.spamhaus.org/pbl/query/PBL1552429

and the instructions:

http://www.spamhaus.org/faq/section/Spa ... 520PBL#197

which points to using authentication, which of course I am. So I understand why my mail provider is rejecting me, but I can’t understand why my password is not being forwarded through the Gargoyle box.

But wait, there’s more…!

This is only a problem when using a Mac, whether it be my wife’s MacBook Pro or my iMac. If I set up the mail clients on Android devices, iPad, Ubuntu/Thunderbird it works fine.

So it seems to come down to how the Mac talks to the Gargoyle box which talks to my mail server.

If anybody can give me some hints on where to next here I would be pleased to hear them.

[ispyisail]

what version of gargoyle?

[PhilthyM]

Oh sorry, 1.6.2 on a TP-Link TL-WR1043N/ND v2

[ispyisail]

Some port or something like that?

Try fail safe reset to clear all settings

http://wiki.openwrt.org/doc/howto/generic.failsafe

[PhilthyM]

Thanks, I tried ports 25 and 1025, their alternate, but no joy there.

I will have a crack at the failsafe stuff on the weekend. Thanks for the tip.

[PhilthyM]

Just been reading about the failsafe mode, I'm not sure what that's going to give me? Assuming it then works, all it will have proved that there is something in Gargoyle that is blocking the password send, but I already know that to be the case!

Sorry if I am sounding dumb, but what would be the purpose of this exercise?

[ispyisail]

Just been reading about the failsafe mode, I'm not sure what that's going to give me? Assuming it then works, all it will have proved that there is something in Gargoyle that is blocking the password send, but I already know that to be the case!

Sorry if I am sounding dumb, but what would be the purpose of this exercise?

same as a factory reset

could be a corrupt config file or you might have accidentally set a wrong setting?

I suspect a blocked port (all outbound ports are open by default) but you might have block one some how?

[PhilthyM]

Thanks for your help and sorry for the slow response, couldn't take the connection off until today - family pressures!

I could not catch the boot sequence properly to go into failsafe mode. So in the end I decided to take a backup and reset the router to the default config. I am guessing that's going to produce the same net effect?

Anyway, I did that and the same problem occurs.

It is clearly something in the Mac that blocks it. If I install Thunderbird under VMWare Fusion on the Mac it works fine. Install Thunderbird natively on the Mac and the password is blocked. I would see this as a Mac problem, except it works through the Untangle firewall/router.

Think I am ready to give up!

[ispyisail]

So in the end I decided to take a backup

If the config file is corrupt you can't use it to restore your setting

You need to start afresh

After a failsafe reset I just first setup the problem area. If that goes well I set up the other stuff.

[PhilthyM]

Thanks for the reply.

Yes, I took the backup, did a "Restore Default Configuration" then made no other changes. From there I tested the email sending and it had the same problem.

Only after that test I restored the config.

I have decided to move mail hosts as I probably should have done years ago anyway. I have a different hosting provider for another domain and they support SSL, which works fine. So that will bypass the problem even though it's not solved!