Outlook sometimes not sending email replies with Avast IS

I’m not sure why this is but every time I installed avast (5 or 6) my Outlook at times will not send a reply. If avast is not installed it never does this. I haven’t seen any threads on this so I’m guessing I’m the only one. I was hoping this update today would fix this.

Any thoughts on this?

Thanks

Any errors displayed in Outlook?

I have the same problem after upgrading to Internet Security 6 and using Outlook 2003. For two of my email accounts, I can receive but cannot send email. The error message says “Outlook is unable to connect to your outgoing (SMTP) server”. I have gone through troubleshooting with my ISP, and they have found nothing on their end that prevents the connection. My laptop was able to ping their server, so contact is happening. I have turned the scanning email functions off and disabled shields and it had no effect. Any advice?

None at all.

I’m using Office 2010 if that helps any.

I had this issue when I tried avast in our church office. The email simply would not work with avast and I was getting your error message if I remember correctly. I really wanted to use avast, but it just would not work. I believe this was a common error as I looked it up and it seemed others were having this problem, but I got found no workaround.

I confirm the same issue with Outlook 2007 on Win Xp sp3.
After sending the email, when it goes to the Outbox, if you open the Outbox folder to make sure the email is being sent from correct account - it will never leave the Outbox folder, i.e. never physically sent out.

I “resolved” the issue by un-checking the “Scan outbound messages” in Mail Shield, which is of course a compromise to the security, but I had the same issue with AVG and already have already lower expectations for security software.

In general, for any email sending/receiving troubleshooting, a screenshot (or at least description) of the account settings in your mail client and a screenshot of avast! mail shield settings - SSL accounts tab are needed. Without any further info, your guess is as good as mine.

If you are implying that everbody has to manually check/match his email account settings in the part of Server Ports in Outlook vs. SSL Accounts in Avast - you may just say so (and that would be helpful). This is easy to check as long as you know that you need to check it.
I assume the two print screens below represent a correct way of setting it up, right?

Your client is misconfigured. Do NOT check the SSL/TLS option in your mail client, leave the ports at normal (25/110/143). Also, delete both accounts from Avast! SSL settings. Now try again. Avast will take care of encryption automatically and add the accounts as needed to its settings.

Really?? Would never guess that following Google’s directions on how to setup Google Mail would lead me to misconfiguration. This is SO contrary to Common Sense, except if Avast is targeting housewives with zero computer knowledge who need a completely automated “black box” type solution that “knows better” than an averagely-educated user.

Yeah really. AVs obviously can’t scan encrypted traffic (encryption wouldn’t be much useful if they could, wouldn’t it ;)) so the communication b/w email client and AV needs to be unencrypted. No blackbox really. Also, this is clearly documented in the avast! help - press F1 on mail shield tab and read it.

Can’t get a good screen shot, but on Outlook these are the settings…
Outgoing server (SMTP) is unchecked.
SSL is unchecked
(SMTP) is set at 25

For avast SSL tab
first Host (Proto)POP3, (Port) 995, (Eccryp) SSL
2nd Host (Proto)SMTP, (Port) 25, (Eccryp) None

Does that help?

Not really with your issue. If you don’t get any errors, I can’t help much really I’m afraid. Test whether you can connect by telnet to the mailserver when you observe the issue (you need to disable the mailshield first). Like this:


telnet mailserver.example.com 25

Should produce something like this in reply:


220 mailserver.example.com ESMTP

The odd thing is it may just be one email that gets stuck. Other replies go out with no trouble, and it is different recipients. This happens about twice a week, maybe three times, with no pattern.

I can copy my reply and just type the address and it will go with no trouble.

Check the email-address when you hit “reply”.

It may be that there is a space in the email adress at the end that you don’t see.

E.g. the correct adress is “Pistol.Pete@Smithandwesson.com” there might be a space at the end making it "Pistol.Pete@Smithandwesson.com ".

Some servers reject that instead of just cutting away the space…

This happens when someone sends you an email with a specified return-address where this space is put in by some kind of copy&paste error.
:wink:

Thanks for the advice. This could be it, but I’m thinking that this has happened even after previous replies to the same person by just hitting “reply.” But it is a possibility so I’ll keep an eye on this.