This discussion has been locked.

You can no longer post new replies to this discussion. If you have a question you can start a new discussion

Error ssl connection to gmail

Hello.
i have recently got a problem with connecting to gmail from my outlook 2007 client. everything has been working nice for a very long time, the settings in outlook are correct. but i receive this error in outlook when connectingnow.

Task '***X@gmail.com - Receiving' reported error (0x800CCC1A) : 'Your server does not support the connection encryption type you have specified. Try changing the encryption method. Contact your mail server administrator or Internet service provider (ISP) for additional assistance.'

i have pop3 proxy enabled in my UTM9. it has always connected ok.
i get a error in live log on utm9:
Fatal: Failed to accept SSL client??

i did not have a problem connecting yesturday.

another thing i have noticed, i never have a count in checked email and email prossessed in log or anywhere else. that means my proxy does not work? or not prossessing any email for virus or spam?

I updated my utm9 to 9.1 a few days ago?? can this be something in this update??

hope someone can answer me on my 2 que[:)]

peter

This thread was automatically locked due to age.

0 Jeff x over 11 years ago in reply to BAlfson

It's starting to make more sense to me but I'm still a little confused.

Some email service providers are very particular about MX records, PTR records, IP addresses and domain names.

If I give the Sophos box the name "sophos.mysite.com" and it's own static IP and PTR record, what IP address will other email servers see when they accept my outgoing mail? Will it be the one tied to mysite.com or sophos.mysite.com? And would that change if I enable or disable the SMTP proxy?

I'm sorry for all of the questions. I'm just not at the level, yet, where I can figure most things out for myself.

--------------------------------------------------------------------
Sophos UTM 9.714-4 - Home User
Currently testing VM on i3-9100 @ 3.60 GHz
16 GB RAM
Dell Optiplex XE
Intel Core 2 Duo CPU E8600 @ 3.33GHz
8GB RAM
--------------------------------------------------------------------
Cancel
Vote Up 0 Vote Down

Cancel
0 BAlfson over 11 years ago

Your server starts an SMTP conversation with HELO sophos.mysite.com, the receiving server does an rDNS lookup and then compares the results to the hostname you announced with your HELO command.

Both mysite.com and sophos.mysite.com would point at the same IP.

If you disable the proxy and the mail server has a hostname of mysite.com, an rDNS PTR containing mysite.com is needed. You can have two PTR records for a single IP.

Cheers - Bob

Sorry for any short responses. Posted from my iPhone.

Sophos UTM Community Moderator
Sophos Certified Architect - UTM
Sophos Certified Engineer - XG
Gold Solution Partner since 2005

MediaSoft, Inc. USA
Cancel
Vote Up 0 Vote Down

Cancel
0 Jeff x over 11 years ago

Bob,

Thanks for all of the info [:)]

Your server starts an SMTP conversation with HELO sophos.mysite.com, the receiving server does an rDNS lookup and then compares the results to the hostname you announced with your HELO command.

If I do not use the SMTP proxy, will my conversation start with HELO mysite.com or will it still be sophos.mysite.com?

Almost all posts I came across, while googling, state multiple PTR records per IP is a bad idea although I don't know why. I'm not sure if Comcast Business will let me have multiple PTR's per IP. I called support but I have to wait for a higher tier tech to call me back with an answer. If I cannot have multiple PTR records per IP, how should I set up Sophos so I can use the SMTP proxy?

--------------------------------------------------------------------
Sophos UTM 9.714-4 - Home User
Currently testing VM on i3-9100 @ 3.60 GHz
16 GB RAM
Dell Optiplex XE
Intel Core 2 Duo CPU E8600 @ 3.33GHz
8GB RAM
--------------------------------------------------------------------
Cancel
Vote Up 0 Vote Down

Cancel
0 Jeff x over 11 years ago

The only critical thing here is that there's a valid rDNS PTR record containing sophos.mysite.com.

Is the "valid rDNS PTR record containing sophos.mysite.com" needed only for the SMTP proxy or for other things?

The MX records for the domains can continue to use mysite.com although sophos.mysite.com would be best practice.

All of my MX records are currently using mysite.com. Is changing them to sophos.mysite.com only necessary if I use the SMTP proxy or should I change them anyway?

--------------------------------------------------------------------
Sophos UTM 9.714-4 - Home User
Currently testing VM on i3-9100 @ 3.60 GHz
16 GB RAM
Dell Optiplex XE
Intel Core 2 Duo CPU E8600 @ 3.33GHz
8GB RAM
--------------------------------------------------------------------
Cancel
Vote Up 0 Vote Down

Cancel
0 William Warren over 11 years ago

gmail isn't pop friendly..they do "support" it but they really prefer IMAP or https.

Owner: Emmanuel Technology Consulting

http://etc-md.com

Former Sophos SG(Astaro) advocate/researcher/Silver Partner

PfSense w/Suricata, ntopng,

Other addons to follow
Cancel
Vote Up 0 Vote Down

Cancel

Error ssl connection to gmail

Submitted a Tech Support Case lately from the Support Portal?