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<div style="font-family:sans-serif"><div style="white-space:normal"><p dir="auto">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).</p>
<p dir="auto">...Peter</p>
<br><p dir="auto">On 23 Sep 2019, at 10:33, rob.mailmate@robertwillett.com wrote:</p>
<blockquote style="border-left:2px solid #777; color:#777; margin:0 0 5px; padding-left:5px"><p dir="auto">Peter,<br>
<br>
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....<br>
<br>
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<br>
<br>
<a href="https://www.privateinternetaccess.com/" style="color:#777">https://www.privateinternetaccess.com/</a><br>
<br>
but thats a guess.<br>
<br>
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?<br>
<br>
Anyway, a quick check on your MX record seems to indicate that you're using Google as your mail provider<br>
<br>
<a href="https://mxtoolbox.com/SuperTool.aspx?action=a%3awinnowmanagement.com&run=toolpage" style="color:#777">https://mxtoolbox.com/SuperTool.aspx?action=a%3awinnowmanagement.com&run=toolpage</a>#<br>
<br>
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.<br>
<br>
What I'd first of all do is:<br>
<br>
Connection to 'whatsmyip.com' and see what IP address you are connecting to that website as. Write the address down.<br>
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.<br>
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.<br>
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.<br>
Post all this into a mail we can see the error you are getting.<br>
Hope this helps.<br>
<br>
Rob<br>
<br>
<br>
<br>
On 23 Sep 2019, at 14:38, Peter Borsella wrote:<br>
</p>
<blockquote style="border-left:2px solid #777; color:#999; margin:0 0 5px; padding-left:5px; border-left-color:#999"><p dir="auto">Hello, Rob,<br>
<br>
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.”<br>
<br>
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.<br>
<br>
If there’s any more details I can provide to assist in trouble shooting this, any help would be greatly appreciated.<br>
<br>
Regards,<br>
Peter<br>
<br>
On 23 Sep 2019, at 9:25, Rob Willett via mailmate wrote:<br>
</p>
<blockquote style="border-left:2px solid #777; color:#BBB; margin:0 0 5px; padding-left:5px; border-left-color:#BBB"><p dir="auto">Peter,<br>
<br>
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.<br>
<br>
Things that come to mind:<br>
<br>
1, As people have already said DNS may be one issue. You already have suggestions for this.<br>
2. It may block outgoing traffic. You need to provide more information on the VPN you use to know if this is an issue.<br>
3. You may your VPN doing some odd routing, so that stuff that should be internal is going externally. Unlikely but seen it happen.<br>
<br>
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 :)<br>
<br>
More information helps here.<br>
<br>
Rob<br>
<br>
On 23 Sep 2019, at 14:08, Peter Borsella wrote:<br>
</p>
<blockquote style="border-left:2px solid #777; color:#BBB; margin:0 0 5px; padding-left:5px; border-left-color:#BBB"><p dir="auto">Thanks for the quick response. I’m not familiar with using this DNS, but now have something to research.<br>
<br>
On 23 Sep 2019, at 9:01, Robert Brenstein wrote:<br>
</p>
<blockquote style="border-left:2px solid #777; color:#BBB; margin:0 0 5px; padding-left:5px; border-left-color:#BBB"><p dir="auto">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.<br>
<br>
On 23 Sep 2019, at 14:41, Peter Borsella wrote:<br>
</p>
<blockquote style="border-left:2px solid #777; color:#BBB; margin:0 0 5px; padding-left:5px; border-left-color:#BBB"><p dir="auto">Good Day, All,<br>
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?<br>
Thanks...Peter<br>
<br>
<br>
Peter Borsella, President<br>
**Winnow Management**</p>
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</blockquote><p dir="auto">Peter Borsella, President<br>
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</blockquote><p dir="auto">Peter Borsella, President<br>
**Winnow Management**<br>
PO Box 1046<br>
Pompano Beach, FL 33061<br>
Office: 954-784-3674<br>
Mobile: 954-253-3761<br>
Fax: 954-301-5829<br>
@pborsella<br>
<br>
Now available, Certified ScrumMaster for Industry! Head to our website for our full class schedule and early registration pricing!<br>
<a href="http://www.winnowmanagement.com" style="color:#999">http://www.winnowmanagement.com</a><br>
<br>
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.</p>
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