Product: Credit card or prepaid card

On or around XX/XX/XXXX, I opened a Southwest credit card that was through Chase. There is a {$140.00} annual fee and one of the perks is that each anniversary year, you are comped for 4 upgraded boardings. 
********* My annual fee was charged on XX/XX/XXXX and on XX/XX/XXXX, an upgraded boarding was posted. There was another one ( for the return flight ) that posted on XX/XX/XXXX. While checking my statement, I noticed the XX/XX/XXXX one had been credited but not the XXXX one. I opened a secure message on XX/XX/XXXX to Chase and asked if someone could clarify why one didn't get credited. 
********* When I received no communication by XXXX, I sent a follow up question asking about the status. What followed was a comedy of errors that was decidedly unfunny. 
********* I received a phone call on XXXX from Chase stating that they needed more information to research my " dispute ''. When I called back, I explained to the rep that I wasn't aware there was a dispute that I was just asking for clarification. She asked for details about why I thought that the charge was supposed to be credited back and she stated I needed to send documentation to prove this claim. After trying to figure out what paperwork I had that Chase didn't already have ( this was THEIR card and THEIR perk ), I tried sending in screenshots of when my annual fee was charged, the date the flight took place, and that I still had ( and to this day still have ) 3 remaining boardings that could be used this year. 
********* After much back and forth, I get a mailed letter that states " this is not something that can be resolved with a dispute ''. The end. No instructions as to who to contact, why they tried opening it as a dispute to begin with, nothing. 
********* On XX/XX/XXXX I called the number on the mailing and asked what the next step was. The rep that I spoke to said they couldn't help because this was handled through XXXX and transferred me to the XXXX XXXX service line. The rep that answered that call was as confused as I was as to why I ended up there and said that I probably needed to talk to XXXX XXXX XXXX, and transferred me there. That rep confirmed what I had thought all along that this was a CHASE card with CHASE perks and CHASE was the one that needed to sort this out. She tried transferring me to a Chase line but it didn't work correctly so she just gave me the number to call. 
********* Calling that number put me in touch with a rep who, upon listening to me tell the same story for the fourth time that day, was apparently very helpful and understanding. He looked into my account history, confirmed my opening date is in XXXX, confirmed that I had slots open for the boarding credits, and that it appeared to just be a slight glitch in the software. I work in the banking industry so this was not an unreasonable assumption. He stated that he was sending my case with the write-up to his marketing team because of my poor customer service experience and I would be getting a letter " shortly '' confirming the credit had been issued. I asked him for a confirmation number or something that could verify that this was going to happen and he said he didn't have that but his name was XXXX and that this was a recorded line so the logs could be pulled ( again, not unreasonable given my experience ). 
********* Fast forward to XX/XX/XXXX when I receive a letter in the mail from Chase stating that the charge stands. Since I didn't get home before their support line closed for the night, I reached out to their help on XXXX who said that they couldn't help because the charge was before my upgraded boardings reset for the year. 
********* I was very annoyed at this point because 1 ) I had someone already confirm that this should have been a credit and 2 ) IF that was the case, that this was before the reset date WHY didn't anyone say that when I asked the FIRST time? Why did I have to go through all the hoops of a dispute that wasn't a dispute? Why couldn't that have been stated by ANYONE I talked to at ANY of the times I called in? 
********* When I saw that Chase was not accredited with the XXXX  and the score they do have is very low, I posted on my XXXX page this morning ( XX/XX/XXXX ) and tagged @ chase. One of their team reached out and said send them a DM and they'd look into it ( same as the XXXX one ). Feeling like I had nothing to lose, I sent them a message. They came back and said they were reaching out to the marketing team and would reply with an update. They finally came back and said the " transactions do not qualify at this time ''. They didn't address the fact that there was ( or least 'should ' be ) a recording of an agent telling me the exact opposite.