My attempts go like this:
Docking request timed out. Please repeat request.
Docking request timed out. Please repeat request.
Docking request timed out. Please repeat request.
Docking request timed out. Please repeat request.
Docking request timed out. Please repeat request.
Docking permission granted. Please proceed to pad 34
PAD LOITERING WARNING
Docking request timed out. Please repeat request.
Docking request timed out. Please repeat request.
Docking request timed out. Please repeat request.
Docking request timed out. Please repeat request.
etc etc.
Yeah this happens to me too. No idea why. Something wigs out in the middle of while i'm docking (I'll be like a minute or two in) then it'll give me a loitering warning, then my request will time out.
Last time right before I was about to land, it was like
Proceed to pad 06
PAD LOITERING WARNING!!!
Docking request timed out. Please repeat request.
Docking request granted. Proceed to pad 06
*literally 10 seconds later*
PAD LOITERING VIOLATION
"wait what?"
Pad loitering violation cleared.
"huh, okay..." *few seconds later*
PAT LOITERING VIOLATION, LETHAL FORCE AUTHORIZED.
"What the FU~~..?!" BOOOM!
and the station opened fire on me, blowing me away in seconds.
Never once was I sure about why this happened.
Every other time its been super smooth, except when weird things start happening the I have to super cruise out and come back... Usually I can dock within 2-3 minutes of granting a request. Its not hard, but I can see this being exorbitantly difficult with digital controls.