My wife and I have been transferring UR points to Southwest and United for a decade. But, more recently, we've run into trouble with "special handling required" messages and, ultimately, Chase outright saying they don't know what's causing the problem and they can't do a manual transfer. They just keep pushing for "trial and error" approaches with name changes on our frequent flyer accounts. I've worked my way up to executive relations and even they seem clueless, today telling me that my inability to transfer from Sapphire Preferred to Southwest RR was because of the middle name on my Southwest credit card - a different card altogether that's not giving me any trouble.

Our frequent flyer accounts all include FIRST MIDDLE LAST. My various Chase credit cards sometimes omit the middle name altogether, some just have a middle initial, and, thanks to a clerical error when we got married, some have a space in our last name (i.e. Mc Donald). We went to the courthouse today to get a corrected marriage certificate.

I've seen varying advice across different forums, such as removing middle names/initials from everything or including the full middle name in everything. And differing answers on whether a space in a last name makes a difference. Am I even able to add my full name to my credit cards if it's 21 characters long (23 including spaces)?

What's the best answer: FIRST MIDDLE LAST on every single frequent flyer and Chase card? Just FIRST LAST on every single account? These name change processes are so cumbersome that we just want to get this right the first time.

EDIT: I should add to this that Global Entry is an issue as well. I need our airline tickets to match my passport exactly, which obviously includes my full middle name.

ONE MORE EDIT: I was able to get my United account changed relatively easily to FIRST MIDDLE LAST (no space in last name). My Chase Sapphire is just FIRST LAST. And, I was able to transfer points instantaneously... so perhaps the middle name isn't so important? BUT I still can't transfer to my Rapid Rewards account even though it's set up exactly the same as United. Now I'm hesitant to change anything since one of the two now works...