I have set up a Cisco IPSec VPN connection instead of using the Cisco client on Mac OS X. I like it fairly well, it just sits in the tray next to the clock and allows me to easily connect and disconnect.

However, the one disadvantage to this is that Apple's network preference pane really enforces the remote server's policy of not storing user passwords, so it will let me store it once when I first create the connection, and it will let me connect with it that way, but after I disconnect it removes the password and won't let me type in that field anymore.

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What I end up with is a box prompting me for login credentials each time I connect. Is there a way to bypass / auto fill this?

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In the bad old days of using Cisco's client, it was easy to edit the .pcf file to work around the remote server policy. Using the alternative client Shimo has worked for me as of a couple of years ago (it's now closed-source, but you can get the old version from Google Code). Here's another workaround I haven't tried that uses the Keychain.

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  • 1
    Thank you. Cisco can be buggy on OS X though and so I much prefer the built in IPSec functionality. Yes with the pcf file you could store the password and make the file effectively "read only" so the client couldn't erase the password even if the remote server's policy said to do so. Also, Shimo might work but really my question is about how to do it on the built-in client. Have tried the workaround - it allows you to store the password initially but after you disconnect the password is erased. – cwd Mar 5 '12 at 1:38
  • @cwd Why did you accept this answer if it doesn't answer your question? Or am I parsing your comment wrong? – unomi Apr 11 '15 at 13:31

There is a workaround with AppleScript that works for me.

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  • Can anyone confirm if this AppleScript still works in 10.9.4? I get my password pasted in the terminal if I run the script via osascript or pasted at the cursor if I run it from AppleScript Editor. – cclark Jul 30 '14 at 6:41
  • Yes it works on 10.9.4. You can also test my fork: gist.github.com/synox/c597321d6d007f812f45 – Synox Sep 12 '14 at 19:15
  • We ended up having it changed on the router to allow it to be saved so unfortunately I no longer have an environment where it is easy to test the fork. Thanks for following up and sharing. – cclark Sep 16 '14 at 4:25
  • Can confirm this works on Yosemite. But it does not seem to automatically enter my password in when I open my VPN connector. It requires me to manually click the "run" button for the script to enter the password in - was this an intended functionality? – theGreenCabbage Dec 8 '14 at 3:12
  • This is not intended, it does all automatically for me. Let me check again with the latest updates. – Synox Dec 8 '14 at 7:28

I got another script on github.

Instead of simulating click and input, this script access the process and simply triggers the actions.

While the first time the script runs, OSX may ask for accessibility.

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  • Sorry total Mac newb here. Does this fire off automatically when I try to connect to my VPN in the top bar or is this called manually sort of like a script to connect to the VPN? – anon58192932 May 22 '15 at 0:18
  • This is giving me 'vpn is now allowed assistive access'. The solution is to go to security settings and add the name of the script to allow access. – anon58192932 May 22 '15 at 18:47

I finally found a working solution. I'm using Anyconnect VPN secure mobility 4.8

We can use this to connect to Anyconnect with terminal

To connect:

printf 'USERNAME\nPASSWORD\ny' | /opt/cisco/anyconnect/bin/vpn -s connect HOST

Replace USERNAME, PASSWORD, and HOST. The \ny at the end is to accept the login banner - this is specific to my host.

Note the single quotes ' instead of double quotes " - this is because double quotes tell Bash to interpret certain characters within strings, such as exclamation marks, as Bash history commands. Double quotes will make this command fail with an "event not found" error if the password contains an exclamation mark. Single-quoted strings pass exclamation marks along without interpreting them.

To disconnect:

/opt/cisco/anyconnect/bin/vpn disconnect

I've made an alias to bash_profile to those commands

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shivam13juna is a new contributor to this site. Take care in asking for clarification, commenting, and answering. Check out our Code of Conduct.


This is caused by a problem with the Keychain Access item for the VPN IPSec connection. A two minute fix will sort it out for you.


  1. Launch Keychain Access by clicking Applications > Utilities > Keychain Access
  2. On the left upper pane, under Keychains select System
  3. On the left lower, under Category select All Items
  4. On the right side of the screen scroll to the bottom and locate the two items called VPN(IPSec)
  5. Double-click the VPN(IPSec) whos kind is IPSec XAuth Password
  6. Click the Access Control button/tab. The applications permitted to use this keychain item will be displayed below. If you’re prompted for your password, enter it.
  7. Click the plus (+) sign
  8. When the Finder window appears, press Cmd + Shift + G on your keyboard
  9. When the Go To Folder dialog appears, enter /usr/libexec/configd and click Go
  10. Select it and click Add
  11. Click Save Changes
  12. Close Keychain Access and try connecting to your VPN again


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  • 2
    doesn't work on high sierra – gabin Jan 11 '18 at 18:19
  • @Gabin you are right, doesn't work on macOS 10.13.3, perhaps you found a working solution? – Darrarski Mar 2 '18 at 13:43
  • @Darrarski unfortunately not. I enter password manually – gabin Mar 2 '18 at 15:16
  • @gabin there is no one "right" answer for this question. As for me - nothing else doesn't work. – skywinder Aug 18 '19 at 9:18
  • did not work for me on Catalina 10.15.4 – jeremyforan May 15 at 14:38

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