Problem sending through proxy

bertradio · 8 Mar 2017, 11:01 PM

I am having failures trying to send emails through smtps-proxy.messagingengine.com

I am running Thunderbird on Win 10 64 bit. I occasionally use Hotspot Shield VPN so I have set TB to use smtps-proxy.messagingengine.com for the outgoing mail server.

Over the past several days, the server has started rejecting some messages. I get a message that the server timed out. If I shift to smtp.fastmail.com the message sends with no problem.

My setup for smtps-proxy.messagingengine.com is port 21, SSL/TLS, Normal password.

This appears to only happen when the message has attachments.

Anyone else have this issue?

BritTim · 9 Mar 2017, 01:28 AM

For information, there is now also a server smtps-proxy.fastmail.com which resolves to a different IP address than smtps-proxy.messagingengine.com. You could try that to see if it resolves your issue.

bertradio · 9 Mar 2017, 02:12 AM

Tried that and got a different error: "The message could not be sent because the Outgoing server (SMTP) smtps-proxy.fastmail.com was lost in the middle of the transaction. Try again."

Is the port setting still 21?

BritTim · 9 Mar 2017, 02:54 AM

Quote:

Originally Posted by bertradio

Tried that and got a different error: "The message could not be sent because the Outgoing server (SMTP) smtps-proxy.fastmail.com was lost in the middle of the transaction. Try again."

Is the port setting still 21?

Are you trying to use SSL or TLS? Afaik all ports should be OK.

Note that you will likely need to use a device password.

bertradio · 9 Mar 2017, 02:58 AM

The choices in TB for connection security are: None, SSL/TLS and STARTTLS.

I have it set to SSL/TLS which was the setting before.

My original settings worked for months. It's only in the last several days that I've had this problem.

bertradio · 9 Mar 2017, 03:07 AM

And I have the same problem whether the VPN is turned on or off.

Terry · 9 Mar 2017, 06:23 AM

Application password ?

https://www.fastmail.com/help/techni...sandports.html

bertradio · 9 Mar 2017, 06:24 AM

The password is fine. The SMTP works fine with emails with no attachments. I have opened a ticket with FM support.

Terry · 9 Mar 2017, 07:29 AM

Try (SMTP) smtps-proxy.fastmail.com with a new application password you old password wont work with fastmail.com
eventually messagingengine.com wont work as they are moving to fastmail.com

bertradio · 9 Mar 2017, 07:39 AM

I had opened a ticket with support.

I just tried again and now it works. Maybe they did something on the server end.

Terry · 9 Mar 2017, 08:00 AM

Wow that was quick, have a look in here it may help down the track.

https://www.fastmail.com/help/clients/apppassword.html

bertradio · 9 Mar 2017, 08:01 AM

I had the right password. That was never the issue because my SMTP settings worked with emails that did not have attachments.

Terry · 9 Mar 2017, 08:12 AM

Yes I read that part, I just thought with all their changes you may have required a new application password....

bertradio · 9 Mar 2017, 08:13 AM

I changed it awhile ago.

Actually after your suggestion I made a new one and it worked. Then I went back to the old one and it worked too. So I think they made some changes on their end.

n5bb · 9 Mar 2017, 09:33 AM

There are other limits which might have prevented sending messages containing attachments due to filenames and quota limits.

The current policy is to limit message size to 70 MB, which means that attachment can't be larger than 50 MB in most cases (due to encoding). It's possible the proxy was set to a lower limit.
You also can't send messages with double extensions such as filename.doc.exe.
You have a quota on the number of messages and the total size of all messages sent in a day, hour, and 10 minutes. For a Basic level account the limits are:
- Daily: 4,000 messages with total size < 1 GB
- Hourly: 2,000 messages with total size <500 MB
- 10 minutes: 1,000 messages with total size <250 MB
- These limits are per recipient. So in 10 minutes you can't send more than 1 message to 10 recipients if the message size (after encoding) was 25 MB for each message (about 18 MB in original file size attachments).
- Other account types have different limits, described in this help page.
- These limits are reset after the appropriate interval. So you might have sent a large attachment to many people in the To, Cc, or Bcc list, then tried sending another message with attachment and been blocked. If you waited an hour or day, the applicable limit would have reset and you can then send again.
If the problem wasn't sending over your quota and was only happening when using the VPN, then it's possible that the proxy server had some setting (such as the TCP MTU size) which was affecting the VPN connection. The VPN changes the packet length and in some cases the MTU (Maximum Transmission Unit) TCP setting might then be a problem.

Bill

8 Mar 2017, 11:01 PM	#1
bertradio Junior Member Join Date: Sep 2016 Posts: 29	Problem sending through proxy I am having failures trying to send emails through smtps-proxy.messagingengine.com I am running Thunderbird on Win 10 64 bit. I occasionally use Hotspot Shield VPN so I have set TB to use smtps-proxy.messagingengine.com for the outgoing mail server. Over the past several days, the server has started rejecting some messages. I get a message that the server timed out. If I shift to smtp.fastmail.com the message sends with no problem. My setup for smtps-proxy.messagingengine.com is port 21, SSL/TLS, Normal password. This appears to only happen when the message has attachments. Anyone else have this issue?

9 Mar 2017, 02:12 AM	#3
bertradio Junior Member Join Date: Sep 2016 Posts: 29	Still get an error Tried that and got a different error: "The message could not be sent because the Outgoing server (SMTP) smtps-proxy.fastmail.com was lost in the middle of the transaction. Try again." Is the port setting still 21?

9 Mar 2017, 09:33 AM	#15
n5bb Intergalactic Postmaster Join Date: May 2004 Location: Irving, Texas Posts: 8,926	There are other limits which might have prevented sending messages containing attachments due to filenames and quota limits. The current policy is to limit message size to 70 MB, which means that attachment can't be larger than 50 MB in most cases (due to encoding). It's possible the proxy was set to a lower limit. You also can't send messages with double extensions such as filename.doc.exe. You have a quota on the number of messages and the total size of all messages sent in a day, hour, and 10 minutes. For a Basic level account the limits are: Daily: 4,000 messages with total size < 1 GB Hourly: 2,000 messages with total size <500 MB 10 minutes: 1,000 messages with total size <250 MB These limits are per recipient. So in 10 minutes you can't send more than 1 message to 10 recipients if the message size (after encoding) was 25 MB for each message (about 18 MB in original file size attachments). Other account types have different limits, described in this help page. These limits are reset after the appropriate interval. So you might have sent a large attachment to many people in the To, Cc, or Bcc list, then tried sending another message with attachment and been blocked. If you waited an hour or day, the applicable limit would have reset and you can then send again. If the problem wasn't sending over your quota and was only happening when using the VPN, then it's possible that the proxy server had some setting (such as the TCP MTU size) which was affecting the VPN connection. The VPN changes the packet length and in some cases the MTU (Maximum Transmission Unit) TCP setting might then be a problem. Bill

9 Mar 2017, 01:28 AM	#2
BritTim The "e" in e-mail Join Date: May 2003 Location: mostly in Thailand Posts: 3,090	For information, there is now also a server smtps-proxy.fastmail.com which resolves to a different IP address than smtps-proxy.messagingengine.com. You could try that to see if it resolves your issue.

9 Mar 2017, 02:58 AM	#5
bertradio Junior Member Join Date: Sep 2016 Posts: 29	The choices in TB for connection security are: None, SSL/TLS and STARTTLS. I have it set to SSL/TLS which was the setting before. My original settings worked for months. It's only in the last several days that I've had this problem.

9 Mar 2017, 03:07 AM	#6
bertradio Junior Member Join Date: Sep 2016 Posts: 29	And I have the same problem whether the VPN is turned on or off.

9 Mar 2017, 06:23 AM	#7
Terry The "e" in e-mail Join Date: Jul 2002 Location: VK4 Posts: 3,012	Application password ? https://www.fastmail.com/help/techni...sandports.html

9 Mar 2017, 06:24 AM	#8
bertradio Junior Member Join Date: Sep 2016 Posts: 29	The password is fine. The SMTP works fine with emails with no attachments. I have opened a ticket with FM support.

9 Mar 2017, 07:29 AM	#9
Terry The "e" in e-mail Join Date: Jul 2002 Location: VK4 Posts: 3,012	Try (SMTP) smtps-proxy.fastmail.com with a new application password you old password wont work with fastmail.com eventually messagingengine.com wont work as they are moving to fastmail.com

9 Mar 2017, 07:39 AM	#10
bertradio Junior Member Join Date: Sep 2016 Posts: 29	I had opened a ticket with support. I just tried again and now it works. Maybe they did something on the server end.

9 Mar 2017, 08:00 AM	#11
Terry The "e" in e-mail Join Date: Jul 2002 Location: VK4 Posts: 3,012	Wow that was quick, have a look in here it may help down the track. https://www.fastmail.com/help/clients/apppassword.html

9 Mar 2017, 08:01 AM	#12
bertradio Junior Member Join Date: Sep 2016 Posts: 29	I had the right password. That was never the issue because my SMTP settings worked with emails that did not have attachments.

9 Mar 2017, 08:12 AM	#13
Terry The "e" in e-mail Join Date: Jul 2002 Location: VK4 Posts: 3,012	Yes I read that part, I just thought with all their changes you may have required a new application password....

9 Mar 2017, 08:13 AM	#14
bertradio Junior Member Join Date: Sep 2016 Posts: 29	I changed it awhile ago. Actually after your suggestion I made a new one and it worked. Then I went back to the old one and it worked too. So I think they made some changes on their end.