I got “Saddle Sore.” I was hopping it would also give me “My Way” but the latter was not triggered.
Ahh apologies, I misread that. So apparently with some you can use non-default aircraft. Interesting!
I just noticed that only 2.6% of players have My Way, so tell you how many people use assists I guess. I’d have thought fewer would use them.
well, I had all assitances off. Started in cold state and finished when the plane was parked, and cold. I also tried to get my way in other flights: Auckland-Sydney. Bogotá-Buenos Aires, Taiwan-Hongkong, using the Fenix a320, FBW a32nx, PMDG 737-700. It just refuses to trigger
Use a default plane. I think it’s been almost proven most achievements require that.
Edit: That may mean standard edition. I had some issues with some achievements using aircraft in the Premium/Deluxe.
Edit 2: Hold a few moments, I’ll check back on my logbook and see what aircraft I used. Should be fairly simple to figure out as long as nothing got deleted 
Ok, my logbook doesn’t quite match my achievement times but maybe that comes down to time zones or something. I either got it using the Boeing 787 on the run for Frequent Flier Miles from LFBD to KSEA or more probably the flight after… Which was the Daher TBM 930 from ZSSS to RKJM which is 322 miles. I rather think it was that one. I doubt I would have tried Frequent Flier without assists.
Finally got “My Way” using a default plane.
Then I started going for “Jack of All Planes.” Unlike stated here, using the Cessna 172 G1000 was the one that got counted (I had to do it twice). However, things took a turn for the worse when I tried the Extra 300. No matter what I do that plane is not counted, I have attempt the with it 4 times with VRF, IRF flights from 260NM up to 310NM and the counter just doesn’t move. And it is not even a plane which is enjoyable to cruise, since it is so unstable.
I had to try several times with that plane too. It did work eventually. I didn’t have any issue cruising, but what bothered me was the airspeed indicator needle is bent slightly! Probably only an issue in VR though 
Very happy and VERY surprised that I finally got my “My way” achievement today! Not sure I did anything significantly different than many previous flights but whatever: it finally unlocked.
Interestingly enough: In this post, Community Manager SeedyL3205 indicated that “… only 0.38% of the 15+ million MSFS players have earned the achievement “My Way””. Not sure where that statistic comes from but it does say a lot as to how challenging it is to get this one to unlock. I am honoured to be a member of this rare club! 
Hello @SlabsFly,
In the Xbox app, it shows the percentage of all players who have unlocked each achievement.
Thanks,
MSFS Team
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I play on Steam and I have all but one achievement. The 1000 hour one. There was times in the past when it didn’t record. My logbook shows well over 1000 in game.
Anyway, the most rare on Steam is .2% with World Traveler and Jack of all Planes. I got them long ago! I’m just hoping I can get the 1000 hr achievement with normal playing before FS2024 launches. I mean without cheating of course 
(loading up slow plane with unlimited fuel, setting autopilot on a 50,000 mile trip and ignoring the computer for a week)
Will old achievements / hours be transferred to fs2024 ?
Would be nice despite its a new sim
Almost certainly no. It’s a new program/sim. I’ve never seen this done before in any franchise.
Thank goodness someone listed all the achievements with an explanation. I am 78 years old and have completed all of them so it can be done on an Xbox S. My big problem was with My Way and Wing Commander. Neither one of them wanted to give you credit for your achievement. My Way I have tried dozens of times with different planes trying to get it to pop. Wing Commander I had to go way over 1000 hours before it would pop. But with ingenuity and a lot of patience, it can be done.
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WOW! 4 years of this post and the achievements are still garbage. I’m with you people. I Keep finishing everything by the book a few different times but not getting credit for them. I reckon a small outfit like Microsoft shouldn’t be expected to get it right after all these years…
It’s still enjoyable to play the simulator but very frustrating at the all too common problems. If anyone has any updated information keep posting! I figure since 2024 is out there is no hope for 2020 now.
Here we are, 2% - the real beta testers of FS24!
(I just got this wonderful achievement. That’s just the total hours in the game I have more than 200… I wonder where the other 150 hours are? Guess for yourself…)
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All achievements should be working normally in 2020 now. The broken ones were fixed some months ago.
So far there’s one broken one in 2024. It’s because 2024 doesn’t record your career missions. The counter remains at 0.
I don’t think it’s counting career mode, but haven’t really paid attn. I’m going through it fast enough it’s working for my purposes Currently at 68%.
You’re right. They should be working.
Not here. I’m flying the same route using the same settings for all planes ad stuck at 70%. Did the Pitts 4 times, CJ4 3 times, TBM 930 5 times, DA62 2 times, G36 3 times. None of these have counted yet. I changed nothing but the type of plane and they’re all default planes. Kinda frustrating. All the others have increased my percentage 5% each as should be.
Probably obvious, but make sure you’re not in dev mode.
You’re working on Jack of all Planes?