Weird delay on transfered calls

I’ve got a FreePBX Distro, PBX running Asterisk 13.29.2, that we noticed if a users transfers calls back in system we have a notable delay (3+ seconds), does anyone have any ideas on how to remedy this? I know adding hops along the way will add something of a delay but this is ridiculous, the guy that originally took the call does not see the delay.

I do want to update this PBX further, but due to it being on Hyper-V it is not in the cards at the moment to take care of.

Anything jumping out at you in the live log during the transfer process that might point to why its failing?
Assuming its not the handsets themselves, when the transfer is attempted, is the live log doing a lot before the transfer process is audibly recognized? Or is it quiet (this is difficult to do on a busy PBX)

What do you mean by that? Is this a normal transfer, or something else?

Also, is the first server in your DNS server list? (In System Admin)

It is, followed by

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