Avatar for Username

Search Support

Avoid support scams. We will never ask you to call or text a phone number or share personal information. Please report suspicious activity using the “Report Abuse” option.

Learn More

This thread was archived. Please ask a new question if you need help.

Can't send MSN email

DeepThought42
DeepThought42
more options

For nearly a year I occasionally had problems sending email on my old Windows XP system. I could “fix” it by making random changes in my settings and putting them back the way they were.

I recently upgraded to a new Windows 7 system [NOT because of the email problem] and was surprised that I still have the same problem. Unfortunately, my “fix” no longer works; I cannot send email at all.

According to “Windows.Microsoft.com”, my Outgoing (SMTP) Server settings should be:

Server address: smtp-mail.outlook.com

Port: 25 (or 587 if 25 is blocked) [I have tried both]

Authentication: Yes

Encrypted Connection: TLS [I have tried STARTTLS and SSL/TLS]

User name: Your email address [xxxxxx@msn.com]

When I attempt to send an email I receive the error message: “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.”

My system consists of:

Windows 7 [updates installed]

Thunderbird v.38.3.0

CenturyLink ISP [1.5 Mbps DSL]

Avast Free 2015 AntiVirus v.10.4.2233 [I have tried turning it off]

Windows Firewall [I have tried turning it off]

CrashPlan Cloud Backup [I have tried turning it off]

Netgear router [no firewall]

ASRock Z97M Pro4 motherboard [Z97 chipset]

Core i3 4170 cpu

I have gone through Mozilla/Thunderbird's forums and help files but the answers tend to revolve around getting the settings right which I believe I am doing [see screenshot]. Obviously I'm doing something wrong. But What?

For nearly a year I occasionally had problems sending email on my old Windows XP system. I could “fix” it by making random changes in my settings and putting them back the way they were. I recently upgraded to a new Windows 7 system [NOT because of the email problem] and was surprised that I still have the same problem. Unfortunately, my “fix” no longer works; I cannot send email at all. According to “Windows.Microsoft.com”, my Outgoing (SMTP) Server settings should be: Server address: smtp-mail.outlook.com Port: 25 (or 587 if 25 is blocked) [I have tried both] Authentication: Yes Encrypted Connection: TLS [I have tried STARTTLS and SSL/TLS] User name: Your email address [xxxxxx@msn.com] When I attempt to send an email I receive the error message: “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.” My system consists of: Windows 7 [updates installed] Thunderbird v.38.3.0 CenturyLink ISP [1.5 Mbps DSL] Avast Free 2015 AntiVirus v.10.4.2233 [I have tried turning it off] Windows Firewall [I have tried turning it off] CrashPlan Cloud Backup [I have tried turning it off] Netgear router [no firewall] ASRock Z97M Pro4 motherboard [Z97 chipset] Core i3 4170 cpu I have gone through Mozilla/Thunderbird's forums and help files but the answers tend to revolve around getting the settings right which I believe I am doing [see screenshot]. Obviously I'm doing something wrong. But What?
Attached screenshots

Modified by DeepThought42

Chosen solution

Thanks to NON over at the AVAST forums, Thunderbird is now working properly!

Thunderbird's SSL certificate for AVAST apparently does not work with the current version of AVAST (10.4.2233).

To quote NON,one must: A) Export the current avast certificate, B) Delete the corrupted avast certificate from Thunderbird, and C) Import the current avast certificate into Thunderbird.

The procedure to do this is: 1) Open Avast Interface -> Settings 2) Select "Active Protection" -> Mail Shield and click "Customize" 3) Select "SSL scanning" and click "Export Certificate" then save it to desktop 4) Run Thunderbird and open Tools -> Options 5) Select "Advanced" -> "Certificate" and click "Show Certificate" button 6) Select "Certificate authority certificate" 7) Find "avast! Web/Mail Shield root" then delete it 8) Click "OK" twice to close "Options" window 9) Follow step 5 & 6 again and import newly exported certificate from step 3 10) Click "OK" twice to close "Options" window

The values which worked for me (Hotmail/MSN/Outlook) were port 25 and STARTTLS. There is a report that this also fixes Thunderbird/AVAST for Gmail users but using SSL/TLS.

I do not understand why turning AVAST off did not work. Perhaps I failed to close and restart Thunderbird?

Read this answer in context 👍 3

All Replies (1)

DeepThought42
DeepThought42 Question owner
more options

Chosen Solution

Thanks to NON over at the AVAST forums, Thunderbird is now working properly!

Thunderbird's SSL certificate for AVAST apparently does not work with the current version of AVAST (10.4.2233).

To quote NON,one must: A) Export the current avast certificate, B) Delete the corrupted avast certificate from Thunderbird, and C) Import the current avast certificate into Thunderbird.

The procedure to do this is: 1) Open Avast Interface -> Settings 2) Select "Active Protection" -> Mail Shield and click "Customize" 3) Select "SSL scanning" and click "Export Certificate" then save it to desktop 4) Run Thunderbird and open Tools -> Options 5) Select "Advanced" -> "Certificate" and click "Show Certificate" button 6) Select "Certificate authority certificate" 7) Find "avast! Web/Mail Shield root" then delete it 8) Click "OK" twice to close "Options" window 9) Follow step 5 & 6 again and import newly exported certificate from step 3 10) Click "OK" twice to close "Options" window

The values which worked for me (Hotmail/MSN/Outlook) were port 25 and STARTTLS. There is a report that this also fixes Thunderbird/AVAST for Gmail users but using SSL/TLS.

I do not understand why turning AVAST off did not work. Perhaps I failed to close and restart Thunderbird?