[MlMt] VPN conflicts

[Peter Borsella]

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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