Emails not always sent but no error shown

G Reading · 18 Feb 2017, 12:28 AM

I am having problems sending emails. This problem has been noticed over the past few weeks but could have been going on longer. When I send an email it goes into the sent folder so it looks like a successful send but it has not gone to the receiver. No error messages are received for the send. Receiving of emails seems to be working correctly. I have started putting my own address as a bcc so that I have a better idea if the message has been successfully sent. If I restart the email client it makes no difference but if I reboot my laptop the new emails will get sent but eventually (within minutes/hours) will not be sent. When it is not sending properly even a simple email sent to myself is not received but shows in the Sent folder.

Current set up:
Win 10, Norton Security, Bell Canada ISP (Sympatico not Fibe), Mozilla Thunderbird (POP3-Port 995 & SMTP-Port 587)

I have tried Windows Live Mail, Opera and eM Client and they all do exactly the same. Win 10 Mail seems to work okay but I wouldn’t want to use it as my everyday email client. I have disabled Norton and it makes no difference. I have used 2 different locations with different routers with no difference.

Berenburger · 18 Feb 2017, 01:15 AM

Quote:

Originally Posted by G Reading

Current set up:
Win 10, Norton Security, Bell Canada ISP (Sympatico not Fibe), Mozilla Thunderbird (POP3-Port 995 & SMTP-Port 587)

I have tried Windows Live Mail, Opera and eM Client and they all do exactly the same. Win 10 Mail seems to work okay but I wouldn’t want to use it as my everyday email client. I have disabled Norton and it makes no difference. I have used 2 different locations with different routers with no difference.

First, welcome to EMD.

Does your ISP has webmail? Does sending work there?

G Reading · 18 Feb 2017, 01:24 AM

Yes it has WebMail and it works but like Win 10 Mail I wouldn't want to use it on a daily basis.
The emails that were not sent properly using Thunderbird etc. do not show up in the Bell webmail. Bell webmail sends ok and the email shows up in the webmail and Thunderbird inbox.

n5bb · 18 Feb 2017, 08:11 AM

I have several troubleshooting ideas, but I warn you that some of these require that many details be carefully followed. I assume that you are using the SMTP server of your ISP to send email.

First start Thunderbird. Go to Help>About Thunderbird. What version are you using? The latest for Windows seems to be 45.7.1.
Activate monitoring tools using both of these:
- Tools>Activity Manager
- Tools>Error Console
- Click Clear in each of these tool windows.
Send an email. Do you see any errors in either window? You will probably see a pop-up showing that the message is being sent, and the Activity Manager may show some green flashing messages. Any messages which remain will probably be green and should not indicate an error.

The next test is much harder to set up and interpret but will tell us many details:

Close Thunderbird (this is very important).
Start a command prompt window. You may be able to do this by right-clicking the Windows icon in the lower left corner and choosing Command Prompt, or if you have a Cortana "Ask me anything" box at the bottom enter cmd and press enter.
Enter the following text in the Command Prompt box. The easiest way is to select all of the text in the box below, then use right-click-Copy, then use right-click-Paste in the Command Prompt box. Then press the Enter key on your keyboard to execute the command.
Code:
```
set NSPR_LOG_MODULES=SMTP:5,TIMESTAMP
```
In a similar fashion, enter the following text in the Command Prompt box and execute it with Enter:
Code:
```
set NSPR_LOG_FILE=%HOMEDRIVE%%HOMEPATH%\Desktop\tbird_log.txt
```
Now type (or copy) this third command in the Command Prompt window and press Enter:
Code:
```
start thunderbird
```
Thunderbird should now be running. It's important that you start it with the command I gave for logging to work.
Send an email with Thunderbird as you would normally. After clicking Send, wait about a minute to be sure the send completes if you have a slow connection or minor errors. Then close Thunderbird (this is very important).
Look on your Windows desktop for a new folder named tbird_log.txt. Double-click this folder to view it in Notepad.

Each line of the log contains a date/time stamp followed by some unimportant labels then a colon:. Most lines then contain SMTP followed by some status information. The first few lines probably look something like this (using the Fastmail SMTP server):

Code:

2017-02-17 23:42:30.209000 UTC - 15652[d11140]: SMTP Connecting to: smtp.fastmail.com
2017-02-17 23:42:30.322000 UTC - 15652[d11140]: SMTP entering state: 0
2017-02-17 23:42:30.322000 UTC - 15652[d11140]: SMTP Response: 220 smtp.fastmail.com ESMTP ready
2017-02-17 23:42:30.322000 UTC - 15652[d11140]: SMTP entering state: 14
2017-02-17 23:42:30.322000 UTC - 15652[d11140]: SMTP Send: EHLO [192.168.1.11]
2017-02-17 23:42:30.368000 UTC - 15652[d11140]: SMTP entering state: 0
2017-02-17 23:42:30.368000 UTC - 15652[d11140]: SMTP Response: 250-smtp.fastmail.com

Eventually you will probably see some steps similar to:

Code:

trying auth method 0x200
SMTP entering state: 16
SMTP AuthLoginStep1() for ......

That is the login to the SMTP server using your password. If this is successful, a few steps later you should see an OK response such as:
Code:
```
STMP entering state: 0
SMTP Response: 235 2.0.0 OK
```
A few steps later you should see the start of the actual email transfer with the From address:
Code:
```
Send: MAIL FROM:<.....> .....
```
And then a few steps later (after an Ok response) you should see the recipient address:
Code:
```
Send: RCPT TO:<......>
```
A few steps later (after another Ok response) you should see the message body, which is only shown in this log as:
Code:
```
SMTP Send:  DATA
```
After the message body is terminated with a . character, you should see QUIT then Bye.
If there is a problem during the SMTP transactions described above, you should see some type of error indicated in the log. For example, if you don't have the correct SMTP submission server name configured in Thunderbird you may not get the ESMTP ready response or you may see errors when the login authentication is performed.
The logging only works when Thunderbird is started from the command line as described. So it won't slow down normal use of Thunderbird and you don't need to remove anything.

Bill

G Reading · 19 Feb 2017, 03:54 AM

Thanks n5bb for such a detailed plan to help resolve my problem. These forums and the people on them are great in their desire to help someone out. I will keep this in mind if I need to do further testing, but I think I have found the cause of my problem. It is not Thunderbird (or Windows Live Mail or eM Client which were also test and exhibited the exact same problem).

I forgot to mention in my original post that I am also using NordVPN and it seems when it is active I have the problem sending emails but have no problem when it is inactive. I have run multiple tests with the same results each time. I have contacted NordVPN and they have made several suggestions; some of which I am already set up for and the others were tried but did not make a difference.

At this point I at least know that if I deactivate NordVPN I will have no problems with sending email.

All my setups in Thunderbird were as they should be and remember I have run the same tests with Windows Live Mail and eM Client and they both exhibited the same problem. As a result of my testing I found that I liked eM Client and have switched over to it as my daily email client. Also as a result of my testing I find sending an auto bcc to myself a useful indicator in verifying email sends and will continue using it.

So at this point I am sure I know the cause but I have no solution. There is a simple solution and that is to only activate NordVPN when I need privacy and inactive when I am sending emails.

n5bb · 19 Feb 2017, 04:42 AM

The VPN may be blocking the SMTP submission port. See if there are other secure SSL ports which your email provider supports. Also see if any firewalls associated with the VPN can be configured to allow the SMTP port you are using. There are other tools which can detect if a port is blocked.

Bill

18 Feb 2017, 12:28 AM	#1
G Reading Junior Member Join Date: Feb 2017 Location: Muskoka, Ont., Canada Posts: 3	Emails not always sent but no error shown I am having problems sending emails. This problem has been noticed over the past few weeks but could have been going on longer. When I send an email it goes into the sent folder so it looks like a successful send but it has not gone to the receiver. No error messages are received for the send. Receiving of emails seems to be working correctly. I have started putting my own address as a bcc so that I have a better idea if the message has been successfully sent. If I restart the email client it makes no difference but if I reboot my laptop the new emails will get sent but eventually (within minutes/hours) will not be sent. When it is not sending properly even a simple email sent to myself is not received but shows in the Sent folder. Current set up: Win 10, Norton Security, Bell Canada ISP (Sympatico not Fibe), Mozilla Thunderbird (POP3-Port 995 & SMTP-Port 587) I have tried Windows Live Mail, Opera and eM Client and they all do exactly the same. Win 10 Mail seems to work okay but I wouldn’t want to use it as my everyday email client. I have disabled Norton and it makes no difference. I have used 2 different locations with different routers with no difference.

18 Feb 2017, 01:24 AM	#3
G Reading Junior Member Join Date: Feb 2017 Location: Muskoka, Ont., Canada Posts: 3	Yes it has WebMail and it works but like Win 10 Mail I wouldn't want to use it on a daily basis. The emails that were not sent properly using Thunderbird etc. do not show up in the Bell webmail. Bell webmail sends ok and the email shows up in the webmail and Thunderbird inbox. Last edited by G Reading : 18 Feb 2017 at 01:46 AM.

18 Feb 2017, 08:11 AM	#4
n5bb Intergalactic Postmaster Join Date: May 2004 Location: Irving, Texas Posts: 8,929	Detailed Thunderbird SMTP debugging I have several troubleshooting ideas, but I warn you that some of these require that many details be carefully followed. I assume that you are using the SMTP server of your ISP to send email. First start Thunderbird. Go to Help>About Thunderbird. What version are you using? The latest for Windows seems to be 45.7.1. Activate monitoring tools using both of these: Tools>Activity Manager Tools>Error Console Click Clear in each of these tool windows. Send an email. Do you see any errors in either window? You will probably see a pop-up showing that the message is being sent, and the Activity Manager may show some green flashing messages. Any messages which remain will probably be green and should not indicate an error. The next test is much harder to set up and interpret but will tell us many details: Close Thunderbird (this is very important). Start a command prompt window. You may be able to do this by right-clicking the Windows icon in the lower left corner and choosing Command Prompt, or if you have a Cortana "Ask me anything" box at the bottom enter cmd and press enter. Enter the following text in the Command Prompt box. The easiest way is to select all of the text in the box below, then use right-click-Copy, then use right-click-Paste in the Command Prompt box. Then press the Enter key on your keyboard to execute the command. Code: set NSPR_LOG_MODULES=SMTP:5,TIMESTAMP In a similar fashion, enter the following text in the Command Prompt box and execute it with Enter: Code: set NSPR_LOG_FILE=%HOMEDRIVE%%HOMEPATH%\Desktop\tbird_log.txt Now type (or copy) this third command in the Command Prompt window and press Enter: Code: start thunderbird Thunderbird should now be running. It's important that you start it with the command I gave for logging to work. Send an email with Thunderbird as you would normally. After clicking Send, wait about a minute to be sure the send completes if you have a slow connection or minor errors. Then close Thunderbird (this is very important). Look on your Windows desktop for a new folder named tbird_log.txt. Double-click this folder to view it in Notepad. Each line of the log contains a date/time stamp followed by some unimportant labels then a colon:. Most lines then contain SMTP followed by some status information. The first few lines probably look something like this (using the Fastmail SMTP server): Code: 2017-02-17 23:42:30.209000 UTC - 15652[d11140]: SMTP Connecting to: smtp.fastmail.com 2017-02-17 23:42:30.322000 UTC - 15652[d11140]: SMTP entering state: 0 2017-02-17 23:42:30.322000 UTC - 15652[d11140]: SMTP Response: 220 smtp.fastmail.com ESMTP ready 2017-02-17 23:42:30.322000 UTC - 15652[d11140]: SMTP entering state: 14 2017-02-17 23:42:30.322000 UTC - 15652[d11140]: SMTP Send: EHLO [192.168.1.11] 2017-02-17 23:42:30.368000 UTC - 15652[d11140]: SMTP entering state: 0 2017-02-17 23:42:30.368000 UTC - 15652[d11140]: SMTP Response: 250-smtp.fastmail.com Eventually you will probably see some steps similar to: Code: trying auth method 0x200 SMTP entering state: 16 SMTP AuthLoginStep1() for ...... That is the login to the SMTP server using your password. If this is successful, a few steps later you should see an OK response such as: Code: STMP entering state: 0 SMTP Response: 235 2.0.0 OK A few steps later you should see the start of the actual email transfer with the From address: Code: Send: MAIL FROM:<.....> ..... And then a few steps later (after an Ok response) you should see the recipient address: Code: Send: RCPT TO:<......> A few steps later (after another Ok response) you should see the message body, which is only shown in this log as: Code: SMTP Send: DATA After the message body is terminated with a . character, you should see QUIT then Bye. If there is a problem during the SMTP transactions described above, you should see some type of error indicated in the log. For example, if you don't have the correct SMTP submission server name configured in Thunderbird you may not get the ESMTP ready response or you may see errors when the login authentication is performed. The logging only works when Thunderbird is started from the command line as described. So it won't slow down normal use of Thunderbird and you don't need to remove anything. Bill

19 Feb 2017, 03:54 AM	#5
G Reading Junior Member Join Date: Feb 2017 Location: Muskoka, Ont., Canada Posts: 3	Thanks n5bb for such a detailed plan to help resolve my problem. These forums and the people on them are great in their desire to help someone out. I will keep this in mind if I need to do further testing, but I think I have found the cause of my problem. It is not Thunderbird (or Windows Live Mail or eM Client which were also test and exhibited the exact same problem). I forgot to mention in my original post that I am also using NordVPN and it seems when it is active I have the problem sending emails but have no problem when it is inactive. I have run multiple tests with the same results each time. I have contacted NordVPN and they have made several suggestions; some of which I am already set up for and the others were tried but did not make a difference. At this point I at least know that if I deactivate NordVPN I will have no problems with sending email. All my setups in Thunderbird were as they should be and remember I have run the same tests with Windows Live Mail and eM Client and they both exhibited the same problem. As a result of my testing I found that I liked eM Client and have switched over to it as my daily email client. Also as a result of my testing I find sending an auto bcc to myself a useful indicator in verifying email sends and will continue using it. So at this point I am sure I know the cause but I have no solution. There is a simple solution and that is to only activate NordVPN when I need privacy and inactive when I am sending emails.

19 Feb 2017, 04:42 AM	#6
n5bb Intergalactic Postmaster Join Date: May 2004 Location: Irving, Texas Posts: 8,929	The VPN may be blocking the SMTP submission port. See if there are other secure SSL ports which your email provider supports. Also see if any firewalls associated with the VPN can be configured to allow the SMTP port you are using. There are other tools which can detect if a port is blocked. Bill