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Opera Email (POP), AVG, and SSL

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Paul Bartlett

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Oct 4, 2012, 5:36:12 PM10/4/12
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Win XP Pro SP3 2GB RAM / O 11.64 b 1403

I have AVG Internet Security 2012, licensed and paid version. By default,
when I use Opera email via POP, AVG will scan incoming mail on port 110.
No problem. As mail comes in, AVG pops up a standard message that it is
scanning the email. (For outgoing SMTP email, my service provider expects
port 587, and I have not changed AVG accordingly. That is another matter
not at issue here.)

However, I would like to use SSL for email. Opera supports TLS seemingly
without difficulty by clicking on the appropriate option under the mail
account. When I do that, AVG complains that it cannot handle encrypted
incoming email. However, AVG Technologies has a webpage concerning email
encryption (SSL) http://www.avg.com/us-en/faq.num-4447 that indicates how
to set things up for SSL. I followed the instructions, both for AVG and
for my Opera mail account. When I do that and Check All with something in
the Outbox and something to come in, nothing happens in either direction.
No error messages, no nothing. The Outbox does not empty, and nothing
comes into the Inbox. The moment I set Opera back to the old settings
(including not using TLS), everything works perfectly again. I just do not
have any SSL encryption.

Being a paid and licensed user, I contacted AVG Support over the telephone
(US support number). The service person, who seemed to be reading off a
script, said that AVG does not work with Opera, but when I pressed her, it
seemed that it is only the SSL within Opera it does not work with. She
said that it only works with Outlook Express, of all things!!! But the
webpage above says nothing about what email clients AVG does or does not
work with concerning SSL email links, and the instructions seem rather
generic.

Has anyone had experience getting AVG Internet Security and Opera to work
together for SSL email? Thanks.

Whiskers

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Oct 4, 2012, 8:23:00 PM10/4/12
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On 2012-10-04, Paul Bartlett <bart...@panix.com> wrote:

[...]

> Has anyone had experience getting AVG Internet Security and Opera to work
> together for SSL email? Thanks.

I haven't - but I'd be surprised if any encrypted stuff could be 'scanned'
usefully. Rather than try to scan incoming email, scan it after it has
been downloaded - it won't be encrypted any more.

--
-- ^^^^^^^^^^
-- Whiskers
-- ~~~~~~~~~~

Paul Bartlett

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Oct 4, 2012, 9:24:24 PM10/4/12
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On Thu, 04 Oct 2012 20:23:00 -0400, Whiskers <catwh...@operamail.com>
wrote:

> On 2012-10-04, Paul Bartlett <bart...@panix.com> wrote:
>
> [...]
>
>> Has anyone had experience getting AVG Internet Security and Opera to
>> work
>> together for SSL email? Thanks.
>
> I haven't - but I'd be surprised if any encrypted stuff could be
> 'scanned'
> usefully. Rather than try to scan incoming email, scan it after it has
> been downloaded - it won't be encrypted any more.

Probably I did not express myself well. (That's no surprise ;) ) My
understanding with regard to SSL and email -- and this is what I took from
the AVG web page that I gave the link to -- is that (for incoming mail,
say) the server encrypts the packets on the communications link. The
client software then decrypts it for use in the client (Opera here). At
that point, *after* the decryption in the SSL process, the malware scanner
(AVG, in this case) would come into play and scan the message, not the
encrypted packets themselves. But I could very well be wrong, I admit. It
is just that AVG does seem to be able to get involved with email and SSL.
The title of the AVG web page is "Creating servers for scanning e-mails in
Personal Email Scanner - SSL communication."

--
Paul Bartlett

Whiskers

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Oct 5, 2012, 3:56:38 PM10/5/12
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The phrase "creating servers" suggests that their scanning software
includes a local proxy email server which you set up (via the malware
scanner software interface) to receive the incoming email, remove the
encryption, and scan it. Your Mail User Agent (in your case, Opera) will
need to be set up to collect those emails from the local proxy email server
rather than from the upstream server.

Paul Bartlett

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Oct 5, 2012, 4:39:08 PM10/5/12
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Thanks very much for the response.

On Fri, 05 Oct 2012 15:56:38 -0400, Whiskers <catwh...@operamail.com>
wrote
(somewhat excerpted for brevity):

> On 2012-10-05, Paul Bartlett <bart...@panix.com> wrote:
>> On Thu, 04 Oct 2012 20:23:00 -0400, Whiskers <catwh...@operamail.com>
>> wrote:
>>
>>> On 2012-10-04, Paul Bartlett <bart...@panix.com> wrote:
>>>
>>> [...]
>>>
>>>> Has anyone had experience getting AVG Internet Security and Opera to
>>>> work together for SSL email? Thanks.
>>>
>>> I haven't - but I'd be surprised if any encrypted stuff could be
>>> 'scanned' usefully. Rather than try to scan incoming email, scan it
>>> after it has been downloaded - it won't be encrypted any more.
>>
>> Probably I did not express myself well. (That's no surprise ;) [...]
>> It is just that AVG does seem to be able to get involved with
>> email and SSL. The title of the AVG web page is "Creating servers for
>> scanning e-mails in Personal Email Scanner - SSL communication."
>
> The phrase "creating servers" suggests that their scanning software
> includes a local proxy email server which you set up (via the malware
> scanner software interface) to receive the incoming email, remove the
> encryption, and scan it. Your Mail User Agent (in your case, Opera) will
> need to be set up to collect those emails from the local proxy email
> server
> rather than from the upstream server.

That is more or less how I understand things. The instructions on the web
page refer to setting up AVG, and then it refers to setting up the mail
agent (Opera, here). Set up the mail account in Opera (or whatever the MUA
is) for POP and SMTP to use the address 127.0.0.1 with port numbers
specified by AVG in the setup of its servers (which include the address of
the upstream server, normally specified in Opera). All in all the AVG
instructions seemed to be fairly thorough, although there was one field in
the server setup screen not described, which I took to be the port numbers
for the upstream server which I normally specify in Opera.

--
Paul Bartlett

Gerald Gruner

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Oct 5, 2012, 4:54:02 PM10/5/12
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Paul Bartlett schrieb am 4.10.12:

> However, AVG Technologies has a webpage concerning email
> encryption (SSL) http://www.avg.com/us-en/faq.num-4447 that indicates how
> to set things up for SSL. I followed the instructions, both for AVG and
> for my Opera mail account.
[...]
> The service person, who seemed to be reading off a script, said that AVG
> does not work with Opera, but when I pressed her, it seemed that it is
> only the SSL within Opera it does not work with. She said that it only
> works with Outlook Express, of all things!

Or maybe the only thing she knows is outlook... ;-)

[...]
> Has anyone had experience getting AVG Internet Security and Opera to work
> together for SSL email? Thanks.

I don't have AVG, but the description sounds like AVG is acting as a sort
of mail relay. I was running a PGP installation that is working in a
similar way. AVG complains that it cannot handle encrypted incoming email
because it can of course not tap a secured connection.

Are you really sure you did everything as described? It is not enough to
click the "secure" option in opera. You'll have to create a new route
*through* AVG as described on the page.

You have a working opera mail configuration.
Did you set up the AVG mail relay ("POP3 - Add new server" in step 3+4)
with the *identical* values for *host* and *port* as the old opera mail? I
think that means "Connection: Secure to regular port".
Did you then setup the "new" opera mail (in step 5) with local host
127.0.0.1 and ports 5300/5400?

It seems like opera was able to connect to the local AVG mail server but
that was empty. Maybe AVG wasn't able to connect to your real mail account?
Doesn't AVG have a logfile or some status output?
What is written there? Did it connect to your mail server?

MfG
Gerald

--
No trees were killed in the sending of this message. However
a large number of electrons were terribly inconvenienced.

Gerald Gruner

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Oct 6, 2012, 6:44:32 AM10/6/12
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Gerald Gruner schrieb am 5.10.12:

> Paul Bartlett schrieb am 4.10.12:

Do you have solved your problem?
If not look at this page.
http://brucejohnson.ca/avg.html
It looks like a step-by-step tutorial...

Paul Bartlett

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Oct 6, 2012, 2:36:15 PM10/6/12
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On Sat, 06 Oct 2012 06:44:32 -0400, Gerald Gruner <gera...@yahoo.de>
wrote:

> Gerald Gruner schrieb am 5.10.12:
>
>> Paul Bartlett schrieb am 4.10.12:
>
> Do you have solved your problem?
> If not look at this page.
> http://brucejohnson.ca/avg.html
> It looks like a step-by-step tutorial...

Sorry I did not get back to this sooner. Thanks for the link. I looked at
the tutorial. I have checked, rechecked, double checked, and triple
checked, both the AVG web page instructions and the tutorial. As far as I
can tell, I am doing everything I should be doing, but I cannot get it to
work, no matter what I do. (Note that I am closing and restarting Opera
whenever I make a change.) The moment I change the account in Opera back
to the way it was, everything works perfectly, and AVG scans the incoming
emails. (There is no log in AVG that I can find which records what is
happening.) I noted that the Johnson tutorial does not give an example for
Opera as such. Perhaps the AVG representative was right and that AVG SSL
simply does not work with Opera. However, I have no idea why that should
be if it works with other MUAs.

--
Paul Bartlett

Gerald Gruner

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Oct 6, 2012, 4:18:59 PM10/6/12
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Paul Bartlett schrieb am 6.10.12:

> On Sat, 06 Oct 2012 06:44:32 -0400, Gerald Gruner <gera...@yahoo.de>
> wrote:
>
>> Gerald Gruner schrieb am 5.10.12:
>>
>>> Paul Bartlett schrieb am 4.10.12:
>>
>> Do you have solved your problem?
>> If not look at this page.
>> http://brucejohnson.ca/avg.html
>> It looks like a step-by-step tutorial...
>
> Sorry I did not get back to this sooner. Thanks for the link. I looked at
> the tutorial. I have checked, rechecked, double checked, and triple
> checked, both the AVG web page instructions and the tutorial. As far as I
> can tell, I am doing everything I should be doing, but I cannot get it to
> work, no matter what I do. (Note that I am closing and restarting Opera
> whenever I make a change.)

I'm pretty sure Opera is not the problem here. I have used opera in a
similar configuration with a PGP-client acting as a relay.

> The moment I change the account in Opera back to the way it was,
> everything works perfectly, and AVG scans the incoming emails.

Of course, then it is unencrypted.
The secured connection must go *through* AVG. AVG plays the "man in the
middle" and accesses your real mail acount by a secured connection,
downloads (and decrypts) the mails, scans them and forwards them locally to
opera.

> (There is no log in AVG that I can find which records what is
> happening.)

There really is not even a status window or something similar?

> I noted that the Johnson tutorial does not give an example for
> Opera as such.

Opera is sadly not the top selling browser. But the principle is the same
for all mail clients. The menu may look different but the values are the
same. POP3 ist POP3.

> Perhaps the AVG representative was right and that AVG SSL simply does not
> work with Opera. However, I have no idea why that should be if it works
> with other MUAs.

I doubt that strongly because opera accesses mail servers like other mail
clients. Again: POP3 is POP3...

Maybe it is only a very small point you are forgetting.
Are you *really really* sure you have set the host and port of your real
mail account in the setup of AVG?
Did you mark the box "activate the server" in the 3rd screenshot in Bruce
Johnsons page?

Did you set the "new" opera mail server account to 127.0.0.1 : 5300 (the
AVG mail proxy/relay address) including your user name and password and to
*not* secure? (I suppose the internal connection opera - AVG is unsecured.)

Paul Bartlett

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Oct 6, 2012, 5:47:27 PM10/6/12
to
I very much appreciate your assistance in all this.

On Sat, 06 Oct 2012 16:18:59 -0400, Gerald Gruner <gera...@yahoo.de>
wrote:

>> As far as I
>> can tell, I am doing everything I should be doing, but I cannot get it
>> to
>> work, no matter what I do. (Note that I am closing and restarting Opera
>> whenever I make a change.)
>
> I'm pretty sure Opera is not the problem here. I have used opera in a
> similar configuration with a PGP-client acting as a relay.

You are probably right. I finally found on an AVG help page that email
scanning as such is supported for a large number of named MUAs, including
Opera, and not just the "big" ones. Probably somehow it is the connection
specifically for SSL.

> The secured connection must go *through* AVG. AVG plays the "man in the
> middle" and accesses your real mail acount by a secured connection,
> downloads (and decrypts) the mails, scans them and forwards them locally
> to
> opera.

Yes, that has been my understanding all along.

>> (There is no log in AVG that I can find which records what is
>> happening.)
>
> There really is not even a status window or something similar?

Not that I can find. There are firewall and malware scanning logs and the
like, but nothing specifically for email (unless it is buried so deeply or
obscurely that it is not obvious).

> Opera is sadly not the top selling browser. But the principle is the same
> for all mail clients. The menu may look different but the values are the
> same. POP3 ist POP3.

>> Perhaps the AVG representative was right and that AVG SSL simply does
>> not
>> work with Opera. However, I have no idea why that should be if it works
>> with other MUAs.
>
> I doubt that strongly because opera accesses mail servers like other mail
> clients. Again: POP3 is POP3...

Agreed.

> Maybe it is only a very small point you are forgetting.

Maybe not forgetting, so much as overlooking or not being aware of
something in the first place. Please see below.

> Are you *really really* sure you have set the host and port of your real
> mail account in the setup of AVG?

This is one place I may have made an error from ignorance. In the AVG
setup, I put in the port numbers that the server expects for my normal
operation: POP=110, SMTP=587 (yes, for this ISP). However, it finally
occurred to me that if I am trying to use SSL between AVG, as a client
proxy, and the server, the port numbers may be different. So I deleted the
servers in AVG and started over. When I recreated them and specified a
secure connection in each, the port numbers were set by AVG to POP=995,
SMTP=465 by default. I fully admit that I do not know what standard or
semi-standard port numbers are used for what. Now see below.

> Did you mark the box "activate the server" in the 3rd screenshot in Bruce
> Johnsons page?

Yes.

> Did you set the "new" opera mail server account to 127.0.0.1 : 5300 (the
> AVG mail proxy/relay address) including your user name and password and
> to
> *not* secure? (I suppose the internal connection opera - AVG is
> unsecured.)

Yes.

After recreating the new AVG servers, I tried going each way one at a time
(i.e., sending POP by SSL and receiving SMTP as usual, and then the other
way around). Now, in either case, a message box pops up that
authentication failed. This is apparently due to a message from the
server, although it is not clear whether the matter is with AVG as a proxy
or with Opera or the connection between them. But at least something is
trying to happen.

Thanks again.

--
Paul Bartlett

Whiskers

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Oct 7, 2012, 9:40:25 AM10/7/12
to
On 2012-10-06, Paul Bartlett <bart...@panix.com> wrote:
> I very much appreciate your assistance in all this.
>
> On Sat, 06 Oct 2012 16:18:59 -0400, Gerald Gruner <gera...@yahoo.de>
> wrote:

[...]

> After recreating the new AVG servers, I tried going each way one at a time
> (i.e., sending POP by SSL and receiving SMTP as usual, and then the other
> way around). Now, in either case, a message box pops up that
> authentication failed. This is apparently due to a message from the
> server, although it is not clear whether the matter is with AVG as a proxy
> or with Opera or the connection between them. But at least something is
> trying to happen.
>
> Thanks again.

It looks as though AVG expects to get the login details for the upstream
server, from (in your case) Opera; so you need to make sure that Opera has
the username and password set up properly. If the upstream server responds
to AVG with an error message, AVG should pass that back to Opera which then
displays it to you.

Also check that the ports which AVG has set up are correct for the upstream
mail server; your email service's web site should specify which settings to
use. Some email servers won't accept an SSL or TLS connection attempt, and
insist on 'STARTTLS' instead.

Gerald Gruner

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Oct 7, 2012, 10:46:25 AM10/7/12
to
Paul Bartlett schrieb am 6.10.12:

> This is one place I may have made an error from ignorance. In the AVG
> setup, I put in the port numbers that the server expects for my normal
> operation: POP=110, SMTP=587 (yes, for this ISP). However, it finally
> occurred to me that if I am trying to use SSL between AVG, as a client
> proxy, and the server, the port numbers may be different. So I deleted
> the servers in AVG and started over. When I recreated them and specified
> a secure connection in each, the port numbers were set by AVG to
> POP=995, SMTP=465 by default. I fully admit that I do not know what
> standard or semi-standard port numbers are used for what. Now see below.
[...]
> Now, in either case, a message box pops up that authentication failed.
> This is apparently due to a message from the server, although it is not
> clear whether the matter is with AVG as a proxy or with Opera or the
> connection between them.

There is a semi-standard. But you have to set the ports your *provider*
uses no matter what it is. If there is an error with the different port and
no error with the previous setting obviously something happended that the
server believed to be correct before.
I am using two providers, one uses the semi-standard ports POP3 995 and
SMTP 465, but the other uses POP3 110 and SMTP 25 for secure and for
unsecure connection. So check the website of your provider what he wants.

One last idea:
Did you try the secure connection with opera *without* AVG? Did it work or
did you get an error, too?
If yes, exactly these values you had set there you'll have to set in the
AVG mail relay's setup and change opera to the local host.
If no, there's your real problem...

As you didn't tell your mail provider and your exact settings and I don't
have AVG, I have no additional idea how to help you. Sorry...

Paul Bartlett

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Oct 7, 2012, 2:16:13 PM10/7/12
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On Sun, 07 Oct 2012 09:40:25 -0400, Whiskers <catwh...@operamail.com>
wrote:

> On 2012-10-06, Paul Bartlett <bart...@panix.com> wrote:
> [trim]
> It looks as though AVG expects to get the login details for the upstream
> server, from (in your case) Opera; so you need to make sure that Opera
> has
> the username and password set up properly. If the upstream server
> responds
> to AVG with an error message, AVG should pass that back to Opera which
> then
> displays it to you.
>
> Also check that the ports which AVG has set up are correct for the
> upstream
> mail server; your email service's web site should specify which settings
> to
> use. Some email servers won't accept an SSL or TLS connection attempt,
> and
> insist on 'STARTTLS' instead.

On the ISP's website I did find that for SSL SMTP connections, the port to
use is SMTP=465, so I suppose the usual port for SSL POP is also the
standard 995, although I did not find that on the site as such. I did send
a message to the ISP's support desk asking about the port numbers. This
being a Sunday, it may be a day or two before I get a reply. When I go
into the mail account on Opera under "Tools," I can specify "Secure
connection (TLS)" without going through AVG as a proxy with no problem. It
is just back to the original issue that, understandably, AVG cannot handle
the SSL-encrypted packets with the "usual" setup. (Incidentally, my ISP is
Panix, http://www.panix.com .)

Paul Bartlett

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Oct 7, 2012, 2:29:37 PM10/7/12
to
Thanks again for the response. I have just replied to Whiskers, and some
of that reply will also be applicable here.

On Sun, 07 Oct 2012 10:46:25 -0400, Gerald Gruner <gera...@yahoo.de>
wrote:

> There is a semi-standard. But you have to set the ports your *provider*
> uses no matter what it is. If there is an error with the different port
> and
> no error with the previous setting obviously something happended that the
> server believed to be correct before.

I got some information off the ISP website and have sent an inquiry to the
support desk.

> I am using two providers, one uses the semi-standard ports POP3 995 and
> SMTP 465, but the other uses POP3 110 and SMTP 25 for secure and for
> unsecure connection. So check the website of your provider what he wants.

Done. SMTP SSL port number seems to be the usual 465.

> One last idea:
> Did you try the secure connection with opera *without* AVG? Did it work
> or
> did you get an error, too?

If I go into the mail account in Opera and specify "Secure connection
(TLS)" without changing anything else, things proceed as normal, except
that AVG, understandably, complains that it cannot handle the encrypted
packets, as it is not involved directly as a proxy to the upstream server.
Other than that, there is no error message about authentication, and the
transfer goes without a hitch.

> If yes, exactly these values you had set there you'll have to set in the
> AVG mail relay's setup and change opera to the local host.
> If no, there's your real problem...

When I specify TLS in Opera, the port numbers (110/587) do not change.
However, putting those into AVG does not work (i.e., apparently no
communication takes place with the upstream server at all). Using 995/465
seems to allow some kind of communication upstream, but there is an
authentication problem.

> As you didn't tell your mail provider and your exact settings and I don't
> have AVG, I have no additional idea how to help you. Sorry...

But I do genuinely appreciate all your assistance to now. My ISP,
incidentally, is Panix, http://www.panix.com . Other settings are generic,
just as the AVG instruction say, together with nothing exotic in Opera (as
specified by AVG for pretty much any MUA).

--
Paul Bartlett
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