Speed dial different behavior on internal call vs external call

If I call from an outside line to an extension lets say 100, and then extension transfers me by pressing lets say button 5 which is configured to transfer to an external phone number, that works, however if I call from another extension to extension 100, and then they press the same button 5 to an external number, it fails.

Any ideas?
Thanks

PBX Version:16.0.40.4
12.7.8-2306-1.sng7
Asterisk Version:18.9
Grandstream phones w/button programmed to transfer and an external number.

Any logs of the failed calls? If I had to guess it would probably be that it’s failing because of the internal caller ID that’s being transferred out over the trunk.

Review what CID you are setting on the Outbound Route that’s used to placed the transferred call.

When transferring the call, my guess is the source extension number (lets say 102) is being passed to ext 100 and then being forwarded out to the real world via SIP

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