We use a pool line to grab an available line to make outgoing calls. We have one phone that when you go to use the pool line it is set to a specific line and if someone is using it, you can't make an outgoing call, even though it's suppose to grab an available line. Any ideas how to fix. Is this a programming issue or something else.

Sounds like programming issue
You didnt say which system
if you have remote maintence ,some one on this board can dial in and fix it for you.

Looks like the key is programmed as a line key not a pooled line button. Look at program 39 on the phone and check how the phone is programmed.

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Our company services all of Orange county...give me a email and we can swing by to program it for you.