Anyone using ExpressVPN on a Mac and iOS devices (or any VPN with "Split tunneling").

01/22/2020 | Terclinger

[BTerclinger]

I am trying to help some family out who want to use a VPN both while on public wifi, and at home for simple privacy from their ISP.

They are using 2 Mac laptops, 2 older iPhones, 2 iPads, and 1 old android phone. They do not need to use every device at the same time. They have Apple email accounts, gmail accounts, and Outlook and Hotmail email accounts; all email accounts are run through OSX Mail and iOS Mail. Whenever the VPN is enabled on the Macs, Microsoft instantly sends warning notices to the Outlook and Hotmail email accounts demanding verification.

User is forced to click on a link in an email from Microsoft (sent before they lock the user out!) to go online, confirm their backup email program, receive another confirmation email sent to that back up account, and copy and paste a passcode.

Until they do that OSX Mail says "can not verify account name or password” for those accounts. The phrase “automatic syncing” shows up on a Microsoft page they are often taken to. This rarely if ever happens when the Macs are offline and IOS devices check the mail. ExpressVPN touts a Split Tunneling feature on Mac and Windows that can allegedly do the following: Allow every application to use the VPN. One or more applications to NOT use the VPN.

One or more applications as the ONLY applications to use the VPN. On the Mac, it makes no difference what Split Tunneling setting is chosen above; if OSX Mail is open when the VPN is enabled, the Microsoft email accounts get unverified. I tried contacting Microsoft and got passed around to people who don't have a clue. ExpressVPN is telling the customer there’s nothing they can do, it’s a Microsoft issue, and “it proves the VPN is working!”

I thought the point of VPN is to help protect web AND email from being snooped on in public WIFI or by an ISP.

Any suggestions (an alternative VPN?) would be gratefully appreciated. 

[BTerclinger]

Understood, but (a) how does that mean the company is really based/controlled by the PRC? (aside from ExpressVPN as you detailed

and(b) isn’t it the case that their paperwork/shell showing them in the BVI is the legal basis that they can avoid keeping and/or providing logs?

[Enlightened1]

Try Virtual shield. It does not seem to do this for the Mac email, but yes it does it to the Outlook.

[Zhang Fei]

[(a) how does that mean the company is really based/controlled by the PRC?]

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The point is that you don’t know. There’s a reason a lot of fly-by-night scammers are based in the Caribbean.

[onona]

I use NORD

[TheBattman]

Paid or free version?

I ask because I believe ExpressVPN’s tech support is connected with their paid service. Not sure what options they offer for Free users.

I have not had this issue with KeepSolid VPN Unlimited.

[TheBattman]

There’s lots of reasons to have multiple email accounts - from personal business vs. personal to my case - where I have an account I use for anything that requires an email address, but I don’t really want to hear from them again (I call it a SPAM Filter).

[BTerclinger]

They are on PAID version of expressVPN

re KeepSolid VPN Unlimited- are any outlook accounts accessed thru Mac Mail while the VPN is enabled?

[BTerclinger]

thx.

[Squantos]

Good recipe for a Mac Pro Laptop is ........

1. Proton VPN , NordVPN or PIA VPN

2. Proton E-Mail

3. Tor Browser setting “safest” ....

4. Tails OS

5. Zero personal data or media on your computer you use for surfing the net

6. WiFi Spoof that changes your MAC address every few minutes

[phs3]

Yes, but for exchange server/ outlook accounts, I use outlook app for that mail. I dont let it intermingle.

[BTerclinger]

Thank you!

[BTerclinger]

thx!

[BTerclinger]

So when you use the Outlook application on Mac with that VPN on, outlook doesn’t break your email connection and demand verification or does it just keep working?

[TheBattman]

I have one outlook account that I access with Apple Mail.

[TheBattman]

From all the research I did when I was contemplating paying for service - the very best VPN (from a privacy perspective) is one that is based in a country that does NOT cooperate with US and other nation’s anti-privacy laws.

Obviously - as the info on ExpressVPN indicates - they are actually a Hong Kong company - thus have tentacles of China wrapped up - so no assurance of any sort of privacy.

A US Based company is still beholden to US laws and subpoena/court order power (including patriot act unconstitutional invasion).

I would have to look back at my notes from over a year ago when I was digging for details about which countries are most VPN friendly.

[TheBattman]

That is the likely scenario when dealing with VPN service. They, by design, reroute your internet traffic through servers and IP addresses that are not logical to your normal location and machine/local IP. So some authentication servers will complain and seek two-factor authentication. I”m not sure there is a total, sure-fire workaround

[TheBattman]

VPN Unlimited is what I use (It’s from a company called KeepSolid).

[Jemian]

You and me both.

[Zhang Fei]

[From all the research I did when I was contemplating paying for service - the very best VPN (from a privacy perspective) is one that is based in a country that does NOT cooperate with US and other nation’s anti-privacy laws.]

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I am worried about one thing alone - hackers getting my information via the free wifi at the airport or the mall. The VPN short circuits that. And when I use a VPN, my primary concern is that the VPN will not route my data streams to hackers or a foreign government. I know AT&T won’t do that. I don’t really give a damn if Uncle Sam wants to look at my stuff. If he’s interested, he’ll put a tail on me, bug my apartment and vacuum up my info from government databases. It’s the havoc from having my data sent to foreign hackers and having loans taken out in my name and my bank and brokerage accounts emptied out that I’m worried about.

[BTerclinger]

And no problem with that outlook account accessed in Apple Mac mail when your vpn is on? Thats the issue I am trying to solve! THANK YOU.