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IPsec on Mac OS X Panther?

ItsMr.Data wants to take a bite out of this issue: "I just got a new PowerBook with Airport. I wish to use it in the wireless network at the university I attend. The problem is that the university uses BlueSocket to secure the WIFI connections. The BlueSocket gateway is configured for IPsec tunnels. The client tool that BlueSocket provides does not work properly under Panther. I was told by the network department that it would be up to me to find a solution until BlueSocket comes out with an updated client. Being a poor college student, I would like to find a cheap or free solution. I have never worked with VPNs or IPsec. Do any Slashdot readers have any good ideas?"

84 comments

  1. Internet Connect by CptChipJew · · Score: 5, Informative

    Can't you use the Internet Connect application that ships with OS X to make an IPSec connection to their VPN? That's how I connect to my school's.

    First post?

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    Vonal Declosion
    1. Re:Internet Connect by Anonymous Coward · · Score: 2, Informative

      My Universety use IPsec and VPN, I use cisco VPN client for OS X.

    2. Re:Internet Connect by Anonymous Coward · · Score: 1, Informative

      cisco makes one, my university uses it...try that out. I dunno how to obtain it if not from your university, but it's ipsec and works under panther

    3. Re:Internet Connect by Anonymous Coward · · Score: 0

      Cisco's VPN program has the worst looking GUI ever. Kerning of the text is unpredictable. Despicable...

    4. Re:Internet Connect by Anonymous Coward · · Score: 0

      i agree. i would like to use the built-in vpn software, not this crap that is cisco! i mean, it works (i'm using it now in my oracle class), but man it is ugly. :(

  2. Poor? by avalys · · Score: 5, Funny

    A new Powerbook? I wish I was a poor college student.

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    This space intentionally left blank.
    1. Re:Poor? by Mariani · · Score: 5, Funny

      Poor after buying a Powerbook.

  3. IPSec should work fine; need config info by anothy · · Score: 4, Insightful

    The IPSec facilities in Panther should be more than sufficient for what you need. In my experience (in very nearly the exact same situation, as well as similar ones at corporation), the hardest part is wrangling the proper information out of your support staff. First you have to find someone who know WTF you're talking about. then they have to find the information. then they (may) have to get approval to give it to you. that generally involves convincing some clueless administrative type that you're not an 3vi1 h4xx0r. and then they have to actually give it to you. and the odds of getting the info right on the first try is not so good.
    my biggest bit of advice is find some friendly, knowledgeable admin, find out what she likes to drink, and buy her lots of it.

    --

    i speak for myself and those who like what i say.
    1. Re:IPSec should work fine; need config info by kerry-buckley · · Score: 5, Funny
      my biggest bit of advice is find some friendly, knowledgeable admin, find out what she likes to drink, and buy her lots of it.
      And hope she doesn't hit you when you admit that you only got her drunk "because you wanted to find out how her tunnel was configured".
    2. Re:IPSec should work fine; need config info by Anonymous Coward · · Score: 0

      but make sure to ask her about the back door

    3. Re:IPSec should work fine; need config info by CuriousGeorge113 · · Score: 1

      OK, so you've established the need to get reliable & useful from the support staff, but gave no insight as to what that reliable & useful information would be?

      How about a clue here, where would we begin, what information do we really need to qrangle here, and why is it so sensitive that the staff would be reluctant to give it up?

      --
      No man is an island, But if you take a bunch of dead guys and tie them together, they make a pretty good raft.
    4. Re:IPSec should work fine; need config info by somethinghollow · · Score: 1

      but gave no insight as to what that reliable & useful information would be.

      If Sys Admins at other colleges are anything like the ones at mine, he doesn't need to list what valuable information they could give you. He doesn't have to because they don't HAVE any reliable or useful information to give. At my university, we had other people that would tell us what we needed to know. Of course, folks in my dorm/honors program were ad hoc administrators of several servers around campus, since the Sys Admins were incompetant...

  4. At Rutgers... by Fuzzle · · Score: 3, Informative

    When I was an organizer with NJPIRG at Rutgers, I used Bluesocket's IPSEC utility with early Developer's builds of Panther and it worked fine. YMMV.

    1. Re:At Rutgers... by Anonymous Coward · · Score: 4, Funny

      That's the thing though. His mileage has varied.

      5, informative?

  5. +1, Funny by anothy · · Score: 1

    wow. where are my mod points when i need them.

    for the record, i wasn't suggesting getting anyone drunk; rather, give it as a gift. given we're talking about techies, maybe a large DIMM or ThinkGeek gift certificate would've been better, but alcohol's always worked well when we needed to grease the wheels with the landlord, or utility guy, or trash collectors, and so on.

    --

    i speak for myself and those who like what i say.
    1. Re:+1, Funny by alaeth · · Score: 3, Funny

      I find Slurpees(Squishees? whatever) and donuts work best. I somehow manage to get a PC upgrade every cycle... my co-workers are mystified ;)

      --
      Sig goes here.
    2. Re:+1, Funny by Anonymous Coward · · Score: 0

      Especially when they come in those winning iTunes cups!

  6. Re:Cisco.. by sinergy · · Score: 3, Informative

    LEAP is proprietary as well. A more open standard is PEAP.

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  7. Re:+5, Funny by Anonymous Coward · · Score: 2, Informative

    Yeah, the first post has a good idea. Use the Internet connection utility. It allows you to create a IPSec connection and is integrated very well with Panther.

  8. Re:Cisco.. by peterjhill2002 · · Score: 2, Informative

    Would that be Microsoft PEAP (PEAP-EAP-MSCHAPv2) or Cisco PEAP (PEAP-EAP-GTC)?

    The lovely thing about open standards is that there can be some many ways to implement them :-p

    Windows ships with a client that supports MS PEAP. The Cisco aironet client supports Cisco PEAP. They are not really compatible. The MS PEAP client works great when authenticating against and NT Domain or an AD. The Cisco version works with more third party radius backends to authenticate clients. Designing a wireless security and authentication infrastructure can be interesting. Particularly if you want to avoid storing cleartext passwords anywhere.

    The Apple Panther client supports L2TP over IPsec. I am not sure what bluesockets is doing with IPsec, but that would be a good thing for them to support.

  9. Re:Cisco.. by grocer · · Score: 1

    LEAP can be configured to work with Airport (I think it works out of the box but not sure). I do know my university uses Cisco LEAP and my iBook works where I can find wireless coverage...

    For reference, I have an iBook G3 with 10.2.8 and the newest Aiport drivers.

  10. Re:Cisco.. by Anonymous Coward · · Score: 0
    LEAP is proprietary as well. A more open standard is PEAP.

    I don't know if I'd say Cisco stuff is proprietary since they're basically THE networking company. Bluesocket stuff is a niche market proprietary thing, but Cisco shit is pretty much standard. I mean for crying out loud, you're not putting netgear access points out there are you?

  11. unfortunately by austad · · Score: 5, Informative

    The IPSec VPN software that is built into panther is missing a lot of features that would make it actually useful. It does not support NAT Traversal, so you can't use it from behind a firewall or NAT device. It does not support XAUTH, which I assume is what your school is using to authenticate you.

    You may be able to use the Cisco VPN client though. The GUI for OSX is fairly unconfigurable, but you can edit the .pcf files that describe the connection manually. Cisco has docs on their site of what each line does. I use the Cisco client under OSX to connect to my Netscreen box at home, and I use it for work too. Although, the Netscreen required messing with the .pcf file.

    --
    Need Free Juniper/NetScreen Support? JuniperForum
    1. Re:unfortunately by azpcox · · Score: 5, Informative

      Although the IPSec VPN client doesn't support NAT traversal, if you have a Linksys or something similar, they have an item called IPSec pass through which will do the NAT (technically there is no port associated with ESP traffic) for you to a single device. The UDP/500 traffic has no problem, just the ESP/AH traffic in certain instances.

      --
      What exactly do you mean by "Don't touch this button?"
    2. Re:unfortunately by MarcQuadra · · Score: 1

      How'd you get the Cisco VPN client working under 10.3? I've had to halt 10.3 rollout at my work because it doesn't work.

      --
      "Sometimes, I think Trent just needs a cup of hot chocolate and a blankie." -Tori Amos on Nine Inch Nails
  12. Re:Cisco.. by sinergy · · Score: 1

    You are right, but that would be a GOOD thing, I'd think.

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    ...
  13. Good luck by cbiagini · · Score: 3, Informative

    I've tried to connect to my school's network, too, with little success. We use Cisco's VPN, and it's the same deal: no Panther-compatible client.

    Best I can do for you is this hint at macosxhints:
    http://www.macosxhints.com/article.php?story=20031 11911433687&query=cisco+vpn

    I tried it, and it didn't work, but who knows...maybe the settings files for your VPN client are similar. Stab in the dark...it's all I got.

    1. Re:Good luck by Anonymous Coward · · Score: 0

      Strange, I'm using the Cisco VPN client on my University's wireless network and it is working fine. You need the latest version. The original one that I had downloaded didn't work.

    2. Re:Good luck by caseih · · Score: 4, Informative

      Cisco's VPN client is very much panther compatible. I use it every day. Just make sure you have the lastest version (version 4.something I believe).

    3. Re:Good luck by cbiagini · · Score: 1

      Sorry for the misinformation, then! I'll give it a shot next time I'm on campus...but I can't seem to find a place that lets you download the 4.0.3 version without being on their network.

    4. Re:Good luck by Glial · · Score: 2, Informative

      4.0.2 And yes, I agree, it is very much Panther compatible.

    5. Re:Good luck by good+soldier+svejk · · Score: 2, Interesting

      I also have no problems with version 3.6 under Panther, connecting to a VPN3005 (IIRC). I use Mathey Wieseck's VPNConnect 1.0.4 GUI.

      --
      It is cowardly, and a betrayal of whatever it means to be a Jew, to act as a white man

      -James Baldwin
    6. Re:Good luck by cbiagini · · Score: 1

      Haha, okay, well then I'm a retard. There's what, five replies so far telling me that I'm wrong?

      I guess I'll have to wait until my university updates the client. As of now, I can still only download the older version.

    7. Re:Good luck by Anonymous Coward · · Score: 0

      The older Cisco clients work as well including 3.7 with Panther including across firewalls ( I connect to the hospital to check CT scans, etc.)

    8. Re:Good luck by thehe · · Score: 2, Informative

      I found the, seemingly, same Cisco VPN Client for OS X that my university provides (v. 4.0.1) freely available on several web pages, of which this is one that seemed to work fine:
      http://portnetworks.com/download.html

      I use the 4.0.1 quite happily on a daily basis, with my university (NTNU in Trondheim, Norway) running IPSec, UDP style.

    9. Re:Good luck by billatq · · Score: 1

      I agree too. However, because it's not "panther compatible", we get to use PPTP which is nicely supported by internet connect.

  14. Corrected Link Here by BoomerSooner · · Score: 0, Offtopic
    1. Re:Corrected Link Here by mgs1000 · · Score: 1

      You mean there is a college at Zero-U?

  15. IPSec VPN and CheckPoint by Anonymous Coward · · Score: 0

    I cant try to connect with the crappy checkpoint firewall in use at the school i work at. I run panther and have tried everything. Apple needs to either update their IPsec implementation. checkpoint is so wack! Anybody have any luck with connecting to a checkpoint firewall vpn?

    1. Re:IPSec VPN and CheckPoint by pillar · · Score: 1

      Several years ago I did work on checkpoint fw-1 and vpn-1, it was alwaya a nightmare. I could never get the vpn-1 stuff to work the way I needed it to......suppsedly it's been improved, however, I have since ditched all ties to checkpoint (thank god).

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      nb
    2. Re:IPSec VPN and CheckPoint by -tji · · Score: 1

      Panther does work with VPN-1.. I am using it.
      But, some of the default configurations might be getting in the way.

      - You must use either Certificates, or "Shared Secret" authentication. (Shared Secret is not the common way to configure users.)

      - If you use Shared Secrets, gateway must be set up to support "Aggressive Mode" IKE negotiations.

      See this page for more information on Check Point and Panther.

  16. Panther Compatibility for Bluesocket IPSec tool by Anonymous Coward · · Score: 5, Informative

    Hello,

    I'm the software engineer responsible for the Mac client for Bluesocket. The client software *should* work with Panther. The client software isn't really client software, however, its just a frontend to the built-in IPSec support that was first made available in 10.2.

    If you're having trouble, you can try emailing support@bluesocket.com. Because it is just a frontend to the built-in support, you can try this on the command line to see if you're logged in:

    $ sudo setkey -D

    Which will print out your tunnel status. If it comes back empty, you're not connected. If you see two tunnels, you're good to go. (the GUI will reflect this as well)

    I just tested it again on my Panther box, and it works OK. As an aside, you can also ask your network admin if they support PPTP. The bluesocket box has PPTP support, and is compatible with Jaguar and Panther's PPTP client.

    Thanks!

  17. VaporSec by cpct0 · · Score: 5, Informative

    I don't have experiece with the other IPSec frontends...

    But I can tell you that Vaporsec works well (http://afp548.com) -- oh and don't download the Jaguar version on the site, download the version in the forums (The major difference between the two are a few applescript bugs of no consequence, but it's nice to have a bug-free system.

    And I suggest you ask your admins for the PRECISE configuration, it's not really easy to implement.

    Mike

  18. Silly Freshman by krray · · Score: 2, Funny

    Back in my day we didn't have all these fancy wireless type connections. We were happy with the new 2400 baud modem pool and ignored the 1200 baud pool. Inside the campus ISN (predates ISDN) was the communication method preferred (with WIRES).

    The problems over the years really haven't changed all that much. My ISN port was @ 9600 baud and I wanted the full 38,400 baud available. Hack in.

    Fortunately the modem pool tied in via ISN -- need a modem? Reset a few ports and take control. Server on campus too busy? Knock 'em all offline. I can even think of a few locks on doors that didn't slow us down. Oh, and when we needed software ... we WROTE IT ourselves.

    Hack on.

    1. Re:Silly Freshman by lullabud · · Score: 2, Funny

      Oh yeah? Well back in the cave man days we didn't even know what wires were, so we HAD to communicate wirelessly. I remember slaving away in front of that fire with that blanket, crafting SSP (smoke signal protocol) packets by hand. Sometimes it would take more than 10 minutes to get an initial ping back because they other side hadn't started their fire yet. Even if they had, it took over a minute just to get an intro line of chat finished. Rain storm? Night time? Don't even bother, your network was down for the count.

    2. Re:Silly Freshman by MalleusEBHC · · Score: 1

      We were happy with the new 2400 baud modem pool and ignored the 1200 baud pool. Inside the campus ISN (predates ISDN) was the communication method preferred (with WIRES).

      Be honest, who else just asked themselves what WIRES was an acronym for?

      Bah, I hope I'm not the only moron who has been up till 5 AM coding all week.

    3. Re:Silly Freshman by BorgCopyeditor · · Score: 2, Funny
      Oh yeah? Well, before the Lord God sorted the primordial muck into water and earth and established the firmament of the heavens to separate the waters above from the waters below, I used to have to ...

      Oh, never mind.

      --
      Shop as usual. And avoid panic buying.
  19. try VPN Tracker by garment · · Score: 3, Informative

    at www.equinux.com. relatively cheap considering ease of use - and they might have a student discount, if you ask (beg).

    1. Re:try VPN Tracker by hankster164 · · Score: 1

      I tried VPN tracker. No go with checkkpoint firewall. even thought their site explains it in plain english. You would have to have shell access to firewall in order to get the firewalls security cert. then you could do VPN.

  20. IPSecuritas by wangooroo · · Score: 4, Informative

    I use IPsecuritas v 1.0.3 http://www.lobotomo.com It works with Panther's built in IPSec "racoon" which is a command line tool. man racoon for more info. IPSecuritas works great and its FREE

  21. Re:Cisco.. by petard · · Score: 2, Insightful

    [sarcasm]I don't know if I'd say Microsoft stuff is proprietary since they're basically THE software company.[/sarcasm]

    Bluesocket is based on open industry standards. Many cisco products also support open standards, but they have been known to work in the odd bit of proprietary crap here and there. Cisco more often just do standards a bit early, before they're widely agreed upon, then bring their system in line with the ratified versions of the standards.

    I suspect IHBT...

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    .sig: file not found
  22. Checkpoint VPN help, anyone? by tholomyes · · Score: 1

    Personally, I am trying to figure out how to get internet connect and CheckPoint to play nice together (L2TP over IPSec). Does anyone know what exactly you have to set up on CP to make this happen? (Or a good resource for this information?)

    Counting the months until we put in a PIX...

    --
    When did the future switch from being a promise to a threat? -C. Palahniuk
    1. Re:Checkpoint VPN help, anyone? by libra-dragon · · Score: 1

      That's funny, I was counting the months until we get rid of our PIXes...

    2. Re:Checkpoint VPN help, anyone? by -tji · · Score: 1

      I don't know if the L2TP config will work.. I briefly tried it, but moved on to straight IPSec since that's what most security products use (L2TP/IPSec is more of a Microsoft thing).

      Check Point and Panther do work together, but there are some caveats which may require cooperation from the VPN admin to work out.

      See this page for more information.

  23. VaporSec is excellent and free by Rufosx · · Score: 1

    I use it for connecting to several networks and it is very good. Works with SonicWalls too, which is nice. It can be a little difficult to setup, mainly because you have to interpret the settings from whatever system they are using to select the right options in VaporSec. Took me awhile to figure out how the settings all mapped across.

  24. About built-in client by Rufosx · · Score: 1

    The built-in IPSec client only works for very simple, very standard IPSec connections (although in the IPSec world, there's no such thing as "very standard"). I've never gotten it to work connecting to any IPSec network, but my clients don't always use the most open solutions, either.

  25. IPSecuritas by Anonymous Coward · · Score: 3, Informative

    If you want a free solution that's actually as configurable as VPN Tracker, check out IPSecuritas (http://www.lobotomo.com). It can be tricky to configure, but we got it to work with our company's Checkpoint VPN without altering anything on the firewall side. It even does DNS settings replacement. Not perfect, but better than anything else I"ve run across.

  26. VPN and IPSec by baddawg65 · · Score: 3, Informative

    I've been using Internet Connect to connect to our school network. If that doesn't work you can use freeware VaporSec (URL: http://www.versiontracker.com/dyn/moreinfo/macosx/ 17212) which is graphical configuration of 'racoon' which is the built-in VPN in Mac OS X. You will need a alot of information from the school's network people to configure this properly.

  27. Re:Cisco.. (P|L)EAP? by lullabud · · Score: 2, Insightful

    Saying that PEAP is a more open standard than LEAP isn't going to help anybody connect to a VPN. WPA, 802.1x authentication and even WEP don't really have anything to do with PPTP or IPSEC VPN's, other than they both use encryption and some of them authenticate by username/password. If this guy's school is using Bluesocket VPN I don't think they're worried about using open standards, they've already dished out the money for this VPN solution and I'm willing to bet they'll stick with it. All that aside, I suppose you are right, LEAP is less proprietary than PEAP, I just don't think it's relevant to this situation.

  28. wow.. all these people need a gui?? by josepha48 · · Score: 1
    I configured ipsec using spdadd and scripts ... Mac uses racoon, and there is a pretty simple configuration file. I'd think that they would tell you what the config file needed to be and say use this config file and change IP addresses.

    It's really not that hard once you understand what ipsec is doing. Go to kame.org

    --

    Only 'flamers' flame!
    Does slashdot hate my posts?

    1. Re:wow.. all these people need a gui?? by sld126 · · Score: 2, Insightful

      Not everybody has the time or interest to learn about what ipsec is. A GUI with an IP, username and password should be ALL that's needed to set up an ipsec tunnel. VaporSec, Cisco clients both give you this. If the sysadmin gives you the right info, should take all of 5 minutes to get connected. Less time than reading the first two pages of kame.org. And then on with your real work.

      Hence the OP.

      --
      You're just jealous because the voices only talk to me.
  29. IPSecuritas by mikeoreilly · · Score: 4, Informative

    Check out IPsecuritas:
    http://www.apple.com/downloads/macos x/networking_s ecurity/ipsecuritas.html

    It has connected to every VPN endpoint/router that I have tried to connect to, with the exception of point to multipoint access. VPN Tracker had to release a new racoon binary to get point to multipoint to work. (This is only an issue if you must connect from a fixed IP address and almost no one does this anymore.)

    The racoon IPSec stack in OSX is based on the kame (kame.org) project. See afp548.com for a writeup on how to get the whole thing working via the command line.

    Remember, IPSecuritas is just a GUI for something already built in to OSX.

  30. Re:+5, Funny by Elwood+P+Dowd · · Score: 3, Insightful

    This "Ask /." is one of the examples of what's great about /.: The author of the relevant software responded.

    And he's at (Score:+5, Informative), you kidder.

    --

    There are no trails. There are no trees out here.
  31. Dear lazy school IT managers by BiOFH · · Score: 2, Interesting

    Stop doing this! Stop putting in measures that limit your students to whatever resource you are most comfortable supporting. It's just plain lazy and uncaring.

    The [Australian] University of Wollongong's ITS department is in the process of doing something similar; installing a wireless system that will lock out Mac users (until someone figures out a way around it). In a school! So anyone who chooses to use a Mac gets callously dismissed with a 'Too bad. Sorry. Go buy a Windows machine.' and that's it. They can't be bothered to support you because they don't care to try.

    It's unconscionable and just plain lazy.

    http://www.uow.edu.au/

    --
    - I am made of meat.
    1. Re:Dear lazy school IT managers by zbaron · · Score: 3, Interesting

      I work for a University further north in Australia and we are installing a wireless network that supports Macs as first class citizens ... it helps a lot that I do all the design work and I have a Powerbook. We are using a Cisco VPN solution as they have an excellent client that supports Mac even if its not pretty and Linux as well.

    2. Re:Dear lazy school IT managers by Anonymous Coward · · Score: 0

      considering the UOW couldn't stop people using the squash courts. I'm sure the solution around the this policy will be found as well.

  32. Re:Intentional Private Sex? by sld126 · · Score: 0, Offtopic

    Here: http://127.0.0.1

    --
    You're just jealous because the voices only talk to me.
  33. ipsec ino by Anonymous Coward · · Score: 0

    http://www.netbsd.org/Documentation/network/ipsec/

  34. Why do I bother? by Anonymous Coward · · Score: 0

    I'm starting to think that slashdot is just another place for people to bitch and moan and attack other people for having a difference in opinion.

    slashdot: news for angry elitist hackers. stuff that might otherwise matter.

  35. Talk to the Dean? by MacFury · · Score: 2, Insightful
    Have you considering meeting with the heads of the school to tell them just how much of a problem this is?

    You would be surprised at how responsive they can be. They typically don't know anything about technology (that's why they hire other people to do that stuff)

    Explain to them that while their solution is good, it falls short on what the university should strive to provide. Tell them that universaly WiFi access helps their current students and increases their attractivness to potential students.

    1. Re:Talk to the Dean? by BiOFH · · Score: 1

      They're quite aware of it. Their response to one unit that recently invested in iBooks and the like was along the lines of 'too bad, this is how it is, buy a PC next time'.

      FWIW, I should note that I don't work there any longer.

      --
      - I am made of meat.
  36. Cisco client GUI wraparound by uncle_s · · Score: 1

    If you want the feature set of the Cisco client, but are afraid of setting it up, go here:
    http://www.versiontracker.com/dyn/moreinfo/macosx/ 17119
    It's called CiscoVPN Frontend and is supposedly a cocoa frontend for the cisco client. Never used it, but maybe it provides the compatibility you need in a candy coated GUI. Good Luck

  37. Cisco IPSec VPN client by sulli · · Score: 1

    I have tested this with a Cisco 3000 server and OS X 10.3. Works fine.

    --

    sulli
    RTFJ.
  38. The wonders of bad moderation by lullabud · · Score: 1

    This is just great. Thanks to the moderators making this tiny, itty bitty nugget of knowledge "informative", regardless of the fact that it has nothing to do with the topic of this thread, Google has now put this as the second result for "PEAP Panther" even though this thread gives no information about PEAP other than the fact that it is a standard. This is an example of why staying on topic is necessary, and moderating on topic is even more important. We all can make the web better, and staying on topic helps us do that.

    1. Re:The wonders of bad moderation by sinergy · · Score: 2, Funny

      And with me typing this reply, it will now probably be the only response when somebody types in "PEAP Panther Chocolate Ovaltine"

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      ...
    2. Re:The wonders of bad moderation by lullabud · · Score: 1

      actually, i doubt you're right, because the specific link for your comments isn't going to have all of the key phrases and links to get a high page rank, but since the post i was complaining about was moderated up enough to have it's text included on the page of the root message which does have all that info, and does have a high page rank, it shows up as #2 in the search.

  39. I just went through the same thing... by -tji · · Score: 1

    I just picked up a new 15" Powerbook (what a great machine), and went through the process of getting it connected to my VPN.. Here are some things I learned along the way:

    - The VPN configurable via the network settings GUI is L2TP over IPSec.. This is the same thing that Windows 2K/XP clients support. But, most security devices (Check Point VPN-1, Netscreen) use straight IPSec. It sounds like Bluesocket wants IPSec.

    - MacOS X comes with IPSec from the KAME (Kah-May, Japanese for 'turtle') project. KAME is very common in *BSD platforms, and I believe it is integrated into Linux kernel 2.6. There is a ton of config/compatibility information available for KAME.

    - Several GUI tools are available to help with VPN setup/usage. VPNTracker, VaporSec, and IPSecuritas. Some VPN vendors, like Cisco and Check Point also have MacOS VPN clients (which are probably expensive)

    - I ended up using a set of Perl scripts I found here. This allows me to see exactly what is going on, and tweak as necessary. (I also posted a few more tips about IPSec setup at that forum)

    - I found the debugging of IPSec sessions to be rather difficult. Without help from the VPN administrator, it can be very difficult to determine what is failing..

    - I was able to get the VPN working when using a "shared secret" configuration for the user. Note that this is NOT the same thing as passwords. Using passwords, SecurID tokens, or other one-way authentication systems require XAUTH or other proprietary mechanisms (like Check Point's Hybrid mode). KAME does not support this. A better option, which will be more secure, is to use certificates for authentication. I haven't gotten around to trying this yet, but I have seen other reports of success.

    - The VPN device had to be configured to enable "Aggressive Mode" in the IKE negotiations.

    - Some NAT gateways will not pass IPSec packets. IPSec uses a different IP protocol, not TCP/UDP. So, many gateways don't know how to NAT it. KAME does not support NAT Traversal (encapsulation of the IPSec packet in a UDP packet), so when setting this up make sure you're not behind a NAT gateway.

    - KAME's configuration requires you to enter your IP address. So, as you move to a new LAN or Wireless Access Point, you must reconfigure and restart the VPN. (This is one reason I used the Perl script I linked above. It determines your current IP address automatically.)