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I don't care if I have to add libraries or build whatever on my end. I'm just hoping since OS X has the foundations of Unix that there's some way to run a Linux or BSD client. Specifically, we need a VPN client that's Mac compatible, and ShrewSoft.com has one for Windows, then another for Linux/BSD, but not for Mac. I'm wondering if I can hack-n-stall it on OS X Lion.

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Why wouldn't you just use the built-in IPsec client? –  Zoredache Feb 12 '12 at 9:19
    
Doesn't support IPSec over UDP which we need, just TCP. –  MarqueIV Feb 13 '12 at 1:07
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3 Answers

up vote 2 down vote accepted

Though it is generally possible to port software from Linux over to a mac, there are some exceptions. Software that requires or links into the kernel generally need to a lot of work to be ported, since they require building a kernel driver. VPN software almost always falls into this category since it needs to hook into the networking stack.

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Well apparently they do have an 'experimental' version they built for Mac, but while I can connect to the VPN using it, I can't actually connect to any of the machines once it's logged on, so there's definitely something screwy going on. Still, you get the vote because of your info about the kernel. After all, while my example was about VPN software, the actual question was about running linux apps on a Mac, and that will help others reading this. –  MarqueIV Feb 13 '12 at 1:06
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Many command line applications compile fine on OS X. Since many of these tools have a larger then usual amount of hardware interaction you may need to edit the config files.

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I know this seems counter-intuitive, but have you thought of running the Windows version of the VPN client, not in a virtual machine, but with Wine for OS X ?

Wine can be a bit of a hit-or-miss solutions at times: some programs won't run no matter how much you cajole them, many run more solidly than they do on Windows. Especially if, as is often the case, the Windows client is more mature than the Linux/BSD version, it may be something worth taking a look at.

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Pretty sure that won't work because Wine runs Windows apps in 'bottles' or miniaturized virtual Windows instances if you will (to over-simplify it.) As such, it doesn't integrate with the core part of OS X networking that it would nee to to make this work. –  MarqueIV Feb 13 '12 at 5:03
    
MarqueIV : Not sure where you're getting your info. Wine uses the native Unix network stack, and WineHQ lists no less than 214 network applications that are "officially" supported at the platinum level. And a quick Google search showed at least one VPN client that is at least semi-sucessful under Wine. –  Dmitri Feb 13 '12 at 16:41
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