Difficult to say without more information. Do you always get errors when sending to specific domains or recipients? If so you could switch on detailed logging while sending a test mail.
Does this happen mainly for messages with big attachments? If so it could be a fragmentation problem. Thomas Stephenson has some good advise regarding this that I've taken the liberty to copy below.
You can test increasing the TCP/IP timeout if you like to. If it works better without giving unnecessary delays in other cases it could be useful. 120 secs is still a reasonable value.
/Rolf
Thomas Stephenson:
A POP3/SMTP transmissions
may fail if the
MTU packet size is so large that a packet is fragmented. In many cases the
receiving system
router blocks the receiving servers "packets fragmented" response to the
sending system
using "MTU Discovery". These oversize packets are not accepted and so are
resent. This
results in a timeout, generally at the end of the message transmission but
it can be anywhere
in the process. You need to reduce the MTU size. Windows defaults to a
1500 MTU and many
routers and DSL connections need 1492. You might simply want to turn off
the MTU Discovery
operation.
You might want to get a copy of SG TCP Optimizer that I find quite handy.
maximum size without fragmentation against specific servers. If will also
make it easy to
adjust the MTU.
And finally, does this computer, by chance, happen to have an NVidia NForce
4 chipset on the
motherboard? If so, many other have had this exact problem, and it turned
out to be an
optimization setting for the built in NIC which caused the problems with
packet fragmentation.
Disabling the advanced optimization capability called "checksum offload"
made all the
problems of sending SMTP mail via WinPMail disappear.
<p>Difficult to say without more information. Do you always get errors when sending to specific domains or recipients? If so you could switch on detailed logging while sending a test mail.</p><p>Does this happen mainly for messages with big attachments? If so it could be a fragmentation problem. Thomas Stephenson has some good advise regarding this that I've taken the liberty to copy below.</p><p>You can test increasing the TCP/IP timeout if you like to. If it works better without giving unnecessary delays in other cases it could be useful. 120 secs is still a reasonable value.
&nbsp;</p><p>/Rolf</p><p>&nbsp;</p><p><i>Thomas Stephenson: </i>
</p><blockquote><div><i>A POP3/SMTP transmissions
may fail if the </i></div><div><i>MTU packet size is so large that a packet is fragmented.&nbsp; In many cases the
receiving system </i></div><div><i>router blocks the receiving servers "packets fragmented" response to the
sending system </i></div><div><i>using "MTU Discovery".&nbsp; These oversize packets are not accepted and so are
resent.&nbsp; This </i></div><div><i>results in a timeout, generally at the end of the message transmission but
it can be anywhere </i></div><div><i>in the process.&nbsp; You need to reduce the MTU size. Windows defaults to a
1500 MTU and many </i></div><div><i>routers and DSL connections need 1492.&nbsp; You might simply want to turn off
the MTU Discovery </i></div><div><i>operation.</i></div><i>
</i><div><i>You might want to get a copy of SG TCP Optimizer that I find quite handy.&nbsp;
</i></div><div><i><a href="http://www.speedguide.net/downloads.php" eudora="AUTOURL">http://www.speedguide.net/downloads.php</a>&nbsp; This little
utility will allow you to test your MTU for </i></div><div><i>maximum size without fragmentation against specific servers.&nbsp; If will also
make it easy to </i></div><div><i>adjust the MTU.&nbsp; </i></div><i>
</i><div><i>And finally, does this computer, by chance, happen to have an NVidia NForce
4 chipset on the </i></div><div><i>motherboard?&nbsp; If so, many other have had this exact problem, and it turned
out to be an </i></div><div><i>optimization setting for the built in NIC which caused the problems with
packet fragmentation. </i></div><div><i>Disabling the advanced optimization capability called "checksum offload"
made all the </i></div><div><i>problems of sending SMTP mail via WinPMail disappear.</i></div></blockquote>