SMTP sending fails (timed out)

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suet_yyp
Posts: 4
Joined: January 4th, 2016, 9:11 am

SMTP sending fails (timed out)

Post by suet_yyp »

Hello!

When trying to send an email I get the error
"Sending of the message failed.
The message could not be sent because the connection to Outgoing server (SMTP) smtp-mail.outlook.com timed out. Try again."

I used Outlook 2010 and switched to Thunderbird, since I got a similar error with Outlook. Till three weeks ago everything was working fine.

I get this with a regular outlook.com account (automatic account setup through Thunderbird) and a custom domain zoho.com account with manual configuration (port 587 and 465).

Getting mail through imap is no problem.

I use Win 7 and the latest Thunderbird. I uninstalled PandaAntiVirus, but that did not help.

Any suggestions? [-o<
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DanRaisch
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Re: SMTP sending fails (timed out)

Post by DanRaisch »

Moving to Thunderbird Support as no bug has been identified here.

What security software is running on that system?
Have you set the anti-virus software to NOT scan outgoing messages?
What specific settings are selected in Thunderbird for the SMTP server for that Outlook account, including server name, port number, and choices for "Connection security" and "Authentication method" under Tools>Account Settings>Outgoing Server (SMTP) (at the bottom of the list of accounts on the left)>*server*>Edit?
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tanstaafl
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Re: SMTP sending fails (timed out)

Post by tanstaafl »

http://kb.mozillazine.org/Hotmail documents the normal Outlook.com settings for Thunderbird

If you are using StartTLS (whats normally recommended) try configuring the SMTP server to use TLS (by selecting SSL/TLS) instead. http://windows.microsoft.com/en-US/wind ... e-from-app claims its supported. It should use the same port (587).
suet_yyp
Posts: 4
Joined: January 4th, 2016, 9:11 am

Re: SMTP sending fails (timed out)

Post by suet_yyp »

Thanks the replies!

I am now running AVG AntiVirus but have not installed the email scanning component.

The outlook.com smtp Server is smtp-mail.outlook.com, Port 587, Authentication: Normal password, Security: STARTTLS
Switching to SSL/TLS did not help.

For the zoho.com account I use exactly the same specifics as described on their homepage: https://www.zoho.com/mail/help/thunderb ... ccess.html
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DanRaisch
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Re: SMTP sending fails (timed out)

Post by DanRaisch »

Do you have your full Outlook email address entered as the User Name for the Outlook SMTP server?
sdhberg
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Joined: November 20th, 2008, 11:21 am

Re: SMTP sending fails (timed out)

Post by sdhberg »

Another data point. This just started happening to me on January 4 as well. I've been using Thunderbird for years and every day. this may be related to latest update, because prior to yesterday I had no problems. The timeout errors started popping up yesterday on all three accounts I was using (work Exchange account, Gmail, yahoo). I've noticed a huge degradation in Thunderbird performance today now back at work with the Exchange server account. No changes were made to any of my account settings or antivirus software.
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DanRaisch
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Re: SMTP sending fails (timed out)

Post by DanRaisch »

Did Thunderbird or your anti-virus or firewall software update to a newer version since January 4?
sdhberg
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Re: SMTP sending fails (timed out)

Post by sdhberg »

Thunderbird is 38.5.0. As far as I can discern no updates to AV or FW software.
gfjd45
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Joined: January 5th, 2016, 1:47 pm

Re: SMTP sending fails (timed out)

Post by gfjd45 »

sdhberg wrote:Thunderbird is 38.5.0. As far as I can discern no updates to AV or FW software.
Hi everybody!
If this can be of any help, I have also noticed SMTP timeout failures when sending with TB 38.5.0 that never happened before the recent upgrade.
This happens with 3 different smtp servers when trying to send HTML formatted email messages containing small sized images (100k range) or attachments: the sending notification works correctly up to 100% then nothing happens until it shows the SMTP timeout message as indicated by suet_yyp above.
NB: I have compacted the relevant files and rebuilt the indexes, but the problem remains.
sdhberg
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Joined: November 20th, 2008, 11:21 am

Re: SMTP sending fails (timed out)

Post by sdhberg »

gfjd45 wrote:
sdhberg wrote:Thunderbird is 38.5.0. As far as I can discern no updates to AV or FW software.
Hi everybody!
If this can be of any help, I have also noticed SMTP timeout failures when sending with TB 38.5.0 that never happened before the recent upgrade.
This happens with 3 different smtp servers when trying to send HTML formatted email messages containing small sized images (100k range) or attachments: the sending notification works correctly up to 100% then nothing happens until it shows the SMTP timeout message as indicated by suet_yyp above.
NB: I have compacted the relevant files and rebuilt the indexes, but the problem remains.
Exactly.
Want solution
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Joined: January 5th, 2016, 3:58 pm

Re: SMTP sending fails (timed out)

Post by Want solution »

I am having this exact same problem as has been described by suet_yyp, sdhberg, and gfjd45.

It is happening on two different computers, both running Thundbird 38.4.0 on Linux. Both computers are configured with 3 or 4 different email accounts (a different set of accounts on the two different computers), and the problem is the same on all mail accounts on both computers.

The problem started recently (couldn't say exactly but it seems like a few weeks at the most).

The nature of the problem is exactly as the others have described and through extensive testing seems to be very consistent. Here's how it is:

Receiving mail works just fine. The problem is with sending mail.

Short messages with no attachments send fine with no problem. But add any but the smallest of attachments (anything more than a few kb in size), and it won't send, giving an error message instead. Also, make the message text very long, and it gives the same error message.

This is the text of the error message:

"Send Message Error
Sending of the message failed.
The message could not be sent because the connection to Outgoing server (SMTP) [the server name, whatever it is, e.g. mx01.kolabnow.com, smtp.comcast.net, or whatever] timed out. Try again."

Most of these mail accounts are using port 587, STARTTLS, Normal Password. I really think it has nothing to do with the server or server settings because it's the same problem with 7 different mail accounts on 5 different servers on 2 different instances of Thunderbird on 2 different computers, and I made no changes to any of the settings prior the start of the problem.

I am also not using any type of antivirus software so this is clearly not the problem.

Really looking forward to getting this solved and will greatly appreciate any help that anyone has to offer.

Thanks!
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DanRaisch
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Re: SMTP sending fails (timed out)

Post by DanRaisch »

I am also not using any type of antivirus software so this is clearly not the problem.
Are you running any firewall software, even Windows built in? Time outs very often indicate a problem on the server side or a security software slowing down the interaction between Thunderbird and the server.

sdhberg, what security software, regardless of its update status, are you running on that system?

suet_yyp, you haven't replied to my question above. "Do you have your full Outlook email address entered as the User Name for the Outlook SMTP server?"
gwj2001us
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Joined: January 5th, 2016, 6:12 pm

Re: SMTP sending fails (timed out)

Post by gwj2001us »

sdhberg wrote:Another data point. This just started happening to me on January 4 as well. I've been using Thunderbird for years and every day. this may be related to latest update, because prior to yesterday I had no problems. The timeout errors started popping up yesterday on all three accounts I was using (work Exchange account, Gmail, yahoo). I've noticed a huge degradation in Thunderbird performance today now back at work with the Exchange server account. No changes were made to any of my account settings or antivirus software.

I too started having this problem yesterday - Absolutely nothing else has changed on my computer - and I've been using Thunderbird for over a year on this computer. One more thing, my wife has an absolutely identical computer in the next office - I mean identical - and her version of Thunderbird has not yet started giving this problem.

I suspect a bug in the new version.
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tanstaafl
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Re: SMTP sending fails (timed out)

Post by tanstaafl »

See http://kb.mozillazine.org/Go_back_to_an ... hunderbird if you'd like to experiment with using an older version of Thunderbird. You could install it in a different directory (it will use the same profile) and chose which version you want to run or you could uninstall the current version and install an older version. Uninstalling doesn't delete your profile (which has your mail, address books, settings, add-ons etc.) but if you're worried back it up first with something like Mozbackup.

I just sent a message with a 1.6MB attachment from my outlook, comcast, zoho, yahoo, gmx, fastmail, and gmail accounts with no problems using TB 38.5.0 under Windows 10. I'm using Windows Firewall (with default settings) and BitDefender Free (it does not know how to scan email) as my anti-virus. There is no other security software running, and no proxies.

I don't have the Lightning add-on installed. Does anybody who is running into this problem have Lightning installed?
Want solution
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Joined: January 5th, 2016, 3:58 pm

Re: SMTP sending fails (timed out)

Post by Want solution »

DanRaisch wrote:
I am also not using any type of antivirus software so this is clearly not the problem.
Are you running any firewall software, even Windows built in?
No, no firewall software at all. This is on Linux, not Windows.
gwj2001us wrote:I too started having this problem yesterday - Absolutely nothing else has changed on my computer - and I've been using Thunderbird for over a year on this computer. One more thing, my wife has an absolutely identical computer in the next office - I mean identical - and her version of Thunderbird has not yet started giving this problem.

I suspect a bug in the new version.
Okay, gwj2001us, since you have two computers, one of which is experiencing the problem and one of which is not, could you please go to Help -> About Thunderbird and tell us, which version of Thunderbird are each of your two computers (the one that is having the problem, and the one that is not having the problem) running? This could be useful, I think. Thanks in advance.

Oh, also, could it be that your wife hasn't sent any messages with attachments lately? My experience is that short messages with no attachments don't trigger the problem. So if you've been sending very long messages or messages with attachments, while she's been sending short messages with no or only very small attachments, that could explain the discrepancy.
tanstaafl wrote:See http://kb.mozillazine.org/Go_back_to_an ... hunderbird if you'd like to experiment with using an older version of Thunderbird. You could install it in a different directory (it will use the same profile) and chose which version you want to run or you could uninstall the current version and install an older version. Uninstalling doesn't delete your profile (which has your mail, address books, settings, add-ons etc.) but if you're worried back it up first with something like Mozbackup.

I just sent a message with a 1.6MB attachment from my outlook, comcast, zoho, yahoo, gmx, fastmail, and gmail accounts with no problems using TB 38.5.0 under Windows 10. I'm using Windows Firewall (with default settings) and BitDefender Free (it does not know how to scan email) as my anti-virus. There is no other security software running, and no proxies.

I don't have the Lightning add-on installed. Does anybody who is running into this problem have Lightning installed?
Yes, both of my computers that are having the problem have Lightning installed.
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