RE PIA, this is news to me, Scott, thank you! (Even shocking, as you
say.). Did you find a VPN service that you found more consistent?
On 23 Sep 2019, at 19:08, Scott wrote:
Hi Peter,
On 24 September 2019, at 0427, Peter Borsella wrote:
Hello, Shoshanna,
I’ve gone ahead and submitted the whitelisting requests to PIA, but
while waiting for that I also ran a quick experiment of simply
changing the VPN server, and voila, my email went out!
Thanks again. More reinforcement is needed, but that’s in
progress.
Whilst we're slightly veering off course from MailMate, I will chime
in here as I went through a similar headache and it might be useful
for those trawling the archives in the future to have something else
to check.
From what you've reported, Peter, my sense is that you MAY have
encountered the same issue I did with PIA, and is part of why I ceased
using them and will not use them again in the future.
PIA does not route all of your packets via the same path.
The destination port plays a part in the routing decisions that PIA
makes for which exit-node to send your VPN'd packets through.
What this means in very simple terms is that even if you're connected
to a PIA endpoint in, say, Ontario, Canada, not all of your network
traffic will *actually* go through PIA's Ontario locations.
Depending on the destination *port* of the activity you are
generating, you may find that PIA will route your traffic via Europe
or some other unexpected destination.
Many of the most popular ports, such as 80 and 443 for web traffic
will definitely go via the advertised endpoint, but, other ports,
including those which may be associated with SMTP and IMAP (such as
for email), or anything running on "non standard" ports, may not be.
I had a very long, and very frustrating, back and forth discussion
with PIA about this, but, this is a feature of their platform.
From what I gathered, it's also somewhat dependent upon the VPN
endpoint you may select...in other words, not all endpoints may do
this destination-port based re-routing of your packets.
Therefore, your disconnecting and reconnecting to another VPN server
could well fit in with the above.
It was actually using MailMate which helped me figure this out about
PIA...whilst trying to connect to some private mail servers, and
running into connectivity and authentication woes, I noticed that the
IP address of the inbound connection was NOT the IP address of my VPN
connection.
If you have your own Internet accessible server, this is pretty
trivial to test yourself - I just ran a tcpdump on my destination
server, and from my PIA VPN'd machine, ran a series of nmap sessions,
for all ports, 1-65535, TCP and UDP.
The results were shocking (horrifying for me), with loads of traffic
being routed via AS43350 (NForce, Netherlands) even though my chosen
VPN endpoint was on the other side of the world - but, again, it
wasn't all ports, but certainly a huge number of them.
Anyway, reading your symptoms made me recall this experience with PIA.
Glad you have a working solution and your email is flowing!
Regards,
Scott
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