What elite status benefit have you never been able to actually use?

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Struggling to use your Frequent Flyer Points?

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Never once made that work. Always told there was no availability even when I was booked in Flex and plenty of seats available for sale. IIRC, you had to keep calling back to request them to check again, which was a hassle - no automatic waitlist like QF points upgrades. Was always frustrated when flying and there were still clearly J seats available despite multiple attempts to use the "free upgrade" benefit.
I always found to and from MEL had the best award availability. We flew ADL-MEL a few times to catch the MEL-PER flight. They were absolutely wonderful flights and the Platinum upgrades were the icing on the cake
 
VA platinum car rental membership benefit to Hertz Presidents Circle - VA claimed I used it but Hertz never changed my membership… followed up multiple times with both parties and ended up writing it off - which seemed strangely appropriate for a rental car.
This.

Had almost exactly the same, except with Hilton for the hotel chain status match benefit.

I went for the match (VA WP to complimentary HH Platinum) ahead of a trip to the US a few years back knowing I was staying at two Hilton properties. The ‘use’ of the benefit was acknowledged on the VA site and by VA staff when queried, but nothing ever made it through to Hiltons system. No benefits received.

Chasing VA up I was pretty much told to pound sand as they had done everything on their side… Hilton agents either had no idea what a ‘Velocity’ was, or cared that VA might have tried to send something to them.
 
QF Lifetime Gold status didn't get me a requested upgrade on either of my flights to Perth last week.
I made the mistake of paying a full economy of $1800 assuming it would help.
Maybe Qantas needs a few more flights, as both of mine were packed.
 
The Frequent Flyer Concierge team takes the hard work out of finding reward seat availability. Using their expert knowledge and specialised tools, they'll help you book a great trip that maximises the value for your points.

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