[MlMt] VPN conflicts

[rob.mailmate at robertwillett.com]

Peter,

You don't need to be a network engineer to get VPN's to work. Indeed my 
78 year old mother recently setup a VPN so she could access location 
restricted TV series content by herself. I have to admit I was a little 
surprised but hey ho....

Anyway the key to getting help is to provide concise (but complete) 
information in as simple a summary as possible. Including specific 
information such as the names of the tool helps, e.g. Private Internet 
Access tool doesn't give much to go on, if I search on that, I get lots 
of VPN's that could be that, but none that is definitely that. I'm 
guessing your service is from

https://www.privateinternetaccess.com/

but thats a guess.

Noe the fact that you have outbound traffic issues makes me assume that 
your network provider is external to your local network, and that you 
possibly use an external mail provider, gmail is a guess but could be 
anything. If I check your website, you're possibly based in Florida but 
originally in Pennsylvania?

Anyway, a quick check on your MX record seems to indicate that you're 
using Google as your mail provider

https://mxtoolbox.com/SuperTool.aspx?action=a%3awinnowmanagement.com&run=toolpage#

Mmm... now Google might have put restrictions on how you access your 
email account and you may have fallen foul of these. I have never used 
Google for email so am now wholly in the dark.

What I'd first of all do is:

Connection to 'whatsmyip.com' and see what IP address you are connecting 
to that website as. Write the address down.
Then fire up your VPN and try and connect to 'whatsmyip.com' again and 
now see what it says. Write the address down. If you can't connect to 
whatsmyip.com then you have an outgoing fault and your VPN isn't working 
properly. You will get a while new IP address if your VPN is working.
Open up a terminal window on your Mac. Got to 
Applications->Utilities->Terminal. Type in nslookup news.bbc.co.uk and 
cut and paste the output to a mail.
If you have no issues connecting to whatsmyip.com, fire up mailmate, 
open up the Activity Window in Windows->Activity viewer and try and send 
an email. If it fails you should get an error log.
Post all this into a mail we can see the error you are getting.
Hope this helps.

Rob



On 23 Sep 2019, at 14:38, Peter Borsella wrote:

> Hello, Rob,
>
> I’m not much of a network engineer, so I’m expecting I’ll need 
> to explore more about what’s going on as I simultaneously learn.  
> I’m encouraged that you find it surprising that I’m having 
> difficulty with my VPN, having thought it was “normal.”
>
> I’m using the PIA (Private Internet Access) tool.  And, my problem 
> is indeed related to outbound traffic, with Mailmate telling me that 
> it can’t send messages, leaving them for re-attempts in my Draft 
> folder.  I then turn on the VPN, close Mailmate, launch again, the 
> mail goes out without a hitch.
>
> If there’s any more details I can provide to assist in trouble 
> shooting this, any help would be greatly appreciated.
>
> Regards,
> Peter
>
> On 23 Sep 2019, at 9:25, Rob Willett via mailmate wrote:
>
>> Peter,
>>
>> Your issue is very unlikely to be Mailmate, but rather how your VPN 
>> is configured. I have 3 VPN providers as I have to have specific ones 
>> for specific clients.
>>
>> Things that come to mind:
>>
>> 1,	As people have already said DNS may be one issue. You already have 
>> suggestions for this.
>> 2.	It may block outgoing traffic. You need to provide more 
>> information on the VPN you use to know if this is an issue.
>> 3.	You may your VPN doing some odd routing, so that stuff that should 
>> be internal is going externally. Unlikely but seen it happen.
>>
>> Your comment that using a VPN and having expected issues is not what 
>> I would expect at all. I would expect configuration issues with 
>> Tunnelblck (which for some reason hates me, mind you I hate it), but 
>> we use hardwired versions of that as well as Bitdefender and 
>> Viscosity. I like Viscosity :)
>>
>> More information helps here.
>>
>> Rob
>>
>> On 23 Sep 2019, at 14:08, Peter Borsella wrote:
>>
>>> Thanks for the quick response.  I’m not familiar with using this 
>>> DNS, but now have something to research.
>>>
>>> On 23 Sep 2019, at 9:01, Robert Brenstein wrote:
>>>
>>>> You may want to try using a different DNS provider when tunneling 
>>>> over VPN, like Google’s 8.8.8.8/8.8.4.4 for example. Some VPN 
>>>> services have their own DNS as an option as well.
>>>>
>>>> On 23 Sep 2019, at 14:41, Peter Borsella wrote:
>>>>
>>>>> Good Day, All,
>>>>> I am using a VPN tool on my Mac, and have experienced as might be 
>>>>> expected that emails do not flow with the VPN active.  However, 
>>>>> are there any settings or workarounds that would still allow me to 
>>>>> keep my VPN turned on while exchanging emails?
>>>>> Thanks...Peter
>>>>>
>>>>>
>>>>> Peter Borsella, President
>>>>> **Winnow Management**
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>>> **Winnow Management**
>>> PO Box 1046
>>> Pompano Beach, FL 33061
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> Peter Borsella, President
> **Winnow Management**
> PO Box 1046
> Pompano Beach, FL 33061
> Office:	954-784-3674
> Mobile:	954-253-3761
> Fax:		954-301-5829
> @pborsella
>
> Now available, Certified ScrumMaster for Industry!  Head to our 
> website for our full class schedule and early registration pricing!
> http://www.winnowmanagement.com
>
> CONFIDENTIALITY:  This email and any associated files contain 
> confidential, proprietary and privileged information and unauthorized 
> disclosure or use is prohibited.  If you received this email in error 
> please notify the sender and delete this email from your system.


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