Is anyone else having issues with the Leviathan Slayer Achievement. I have ran the race five times with the time being under 8 minutes with the Ford Fiesta ST RX43 and the achievement still hasn’t popped up. Any help would be appreciated.
Same here, I have done it 4 times, Stock then tuned, Still nothing. Annoying
I think you have to use a player made route.
Its happened to me until I cleared the cache. Then both this one and the Kraken popped up while the game was loading.
Turn off your xbox, then hold down the power button to turn it back on. Hold it for 10 seconds or so will erase the cache
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Confirmed, this workaround works. I got the Leviathan achievement right after I did the clear-cache trick & launched the game & waited for it to put me in freeroam. Next I beat Kraken and did NOT get the achievement. So I shutdown and did the clear-cache trick again. This time the achievement didn’t pop in-game, but I did see it register on my achievements list (from Xbox dashboard).
Note that the instructions above aren’t exactly right (at least not for the original Xbox One … maybe it’s true for the S or X?). Holding down the button for 10 seconds does NOT start the Xbox. What I did was hold down the button for 10 seconds and then let go, saw nothing happening, and then pressed it like normal. That normal press is what started the Xbox.
Regardless, thanks DaReoCharmer for the workaround, I bet that has helped a lot of people 
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Its an annoyance, not really a big deal but those things should pop up with no issues. Yet it keeps happening on multiple goals, not getting the alerts
I am having the same issue, did it in 7:52 and no achievement.
Read the above post and reset your Xbox. It should pop up when you turn it back on.
Thank you to everyone that replied. I did the clear the cache trick and got the achievement to pop up. Now it’s on to trying to get that Peel P50 Trailblazing Achievement.
just finished all the expansion achievements last night, the kraken and leviathan achievements popped for me even though I didn’t clear the cache, all I did was leave the game and come back. the p50 achievement wasn’t as hard as I thought it would be, just have to take the dirt path through the forest and youre good
I’m glad that this issue has been resolved through a hard reset of the Xbox.
If anyone else continues to have this issue or hard resetting/clearing the cache doesn’t do anything. Please submit a ticket here
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Not fixed, I did the race clearly under 8min, no achivement… Before I had not got the kraken either so I did hard reset and the kraken popped up, but not the Leviathan slayer.
EDIT:
My bad, I had the wrong fiesta
I just did it first attempt no issues whatsoever… for Leviathan anyway …still to attempt Kraken
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go on try this 1st… did the clear the cache trick and got the achievement to pop up…(hard resetting/clearing the cache) 
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Can you hit this time in Rivals and still have the Achievement pop? I did a full power-down and restart, but I did not do the button-holding cache-clearing trick yet. I’ve met the time for both Kraken and Leviathan, but I did them in Rivals, not regular racing.
Reset worked for me.