When I'm connected to a Windows XP computer from my Mac OS X 10.6 using the Citrix ICA Client, it seems that the shift key only works for the first letter typed after pressing shift. In order to type multiple uppercase letters, like ICA, I must either press caps lock, or press and release shift before each character.

I've tried switching between standard and enhanced keyboard, as well as the 'Send Special Keys Unchanged' option, but none of these seem to affect the issue. The problem doesn't occur when I switch from the Citrix window to a regular Mac window.

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I found on the Windows computer, I needed to go launch "Remote Desktop" and do the following:

When the Remote Desktop Connection screen opens, click on Options and then the Local Resources tab (right). In the Keyboard section, click the drop down menu arrow and select “On the local computer”. Then click on the General tab, followed by Save As.. and save your settings as “Default.rdp”. This will fix the “sticky keys” issue for both REMOTE DESKTOP and the Remote Desktop - RDP application.

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Found the issue documented on the citrix site. Answer is as above.

http://support.citrix.com/article/CTX110281

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