[MlMt] VPN conflicts

Peter Borsella peter.borsella at winnowmanagement.com
Mon Sep 23 14:29:07 EDT 2019


Hi, Rob,

I just sent an update addressing Shoshanna that a simple change of the 
VPN server in the PIA app did the trick.  However, I’d like to 
continue researching how all of this is set up, so I greatly appreciate 
all of the information you yourself have provided.

Regards,
Peter

On 23 Sep 2019, at 11:34, rob.mailmate at robertwillett.com wrote:

> Peter,
>
> All of the information about you was found in two quick web addresses 
> checks.
>
> I can see that somebody else already runs PIA, so I'd suggest you 
> follow their advice first and if that doesn't work, then do my stuff. 
> The fact it works for another person manes it should work for you.
>
> Let us know how it goes.
>
> Rob
>
> On 23 Sep 2019, at 15:54, Peter Borsella wrote:
>
>> Thank you gain, Rob.  Your quite the detective, and I’m sorry about 
>> not giving more details.  Your guess is right about the PIA tool, and 
>> you’re also on the money about Gmail as Florida.  I’ll go ahead 
>> and run your additional investigative steps and get the results 
>> posted.  It may take me a bit of time (I’m also simultaneously 
>> working).
>>
>> ...Peter
>>
>>
>> On 23 Sep 2019, at 10:33, rob.mailmate at robertwillett.com wrote:
>>
>>> 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**
>>>>>>> _______________________________________________
>>>>>>> mailmate mailing list
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>>>>>>> https://lists.freron.com/listinfo/mailmate
>>>>>>
>>>>>> 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
>>>>>>
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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.
>>
>> 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.

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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