I’m sorry if this has been asked before. I skimmed Reddit briefly for posts on this and saw a few but still a bit confused. Can I use a personal VPN subscription (currently installed on my personal Iphone and MacBook) to connect to my work VPN (installed on my dell work hard drive (fyi I use dell/windows monitors, no desktop computer or laptop)? If so, how?
Yes a tunnel over a tunnel should be technically feasible but for most people it’s unnecessary and not common enough to be supported in a regular way.
The easiest way to do this is probably to use a separate device to add one layer of vpn, then use your work vpn on the computer itself. So for example if you had a router sending traffic through a vpn, then you connected to another vpn using a computer connected to that router, that would work. Though performance is dinged by a vpn, so it would be even worse through two vpn tunnels.
Doing it on one device will be complex. Probably not something you’re going to have an easy time with.
Are you hoping to work remotely from another country? 
Can I use a personal VPN subscription (currently installed on my personal Iphone and MacBook) to connect to my work VPN
No
If so, how?
Your employer IT needs to issue you credentials and VPN software they use to allow you to remote in. Smart IT people do not allow personal devices to remote it.
I was asked to install a handful of apps on my phone device when I started the job - ranging from an expense reimbursement app to MFA app to gmail and more. Should I be concerned re what you say in the last paragraph?
Maybe 
. For various reasons I don’t feel like listing, I’m not going to bother asking my shit HR. Think it’s OK anyway for a few months, plus I’m already remote. Thanks for your input!!
Hello, I have a similar question. I work remote, but only allowed to work inside my country because of our VPN. In theory, could I purchase my own VPN and work outside of the country without causing any security issues?
You might in that case check out Invizbox.
Edit: they I think generally limit it to 90 days but for cell service check out Google Fi. I’ve been a nearly constant international traveler for almost 10 years. They’re by best travel tip.
Never heard of either so thanks for the note. Will check them out…