Edit: I just remembered a totally silly travel situation during my academic career. The school sent me to an academic conference in an interesting location, and I wanted to stay for an extra week to do some touristing. (It was during summer vacation, and golly do I miss those.)
No one had any problem with it, and they told me standard practice was for me to call the airline and pay the $250 (or whatever it was) change fee. No problem, until I noticed that tickets with the new return date would be something like $400 less than the original dates. No tickets had yet been purchased, so I suggested that they buy me those dates directly: everyone would win.
Except... "Sorry, we can't do that." Huh? "Travel must be +/- 2 days of the conference dates."
I presented the situation to my department chair, hoping for an intervention, but she sighed, and said that those people were impossible to deal with. "But, it's the end of the fiscal year, and I have some extra budget [somewhere], so submit a reimbursement form for the $250, and I'll sign it."
Silly, right?