"Loot 2 neutral carepackages" challenge not properly tracking

Product: Apex Legends
Platform:Microsoft XBOX One
Please specify your platform model. Microsoft Xbox One
What is your gamertag/PSN ID/EA Account name? vxxTheGoatxxv
Please provide your squad mates' gamertag/PSN ID/EA Account name if possible. yOuNg Beloved
Are you using any software with an overlay? No
Which Legend were you playing (if applicable)?
Which Legends were your squad mates using (if applicable)?
Where did the issue occur? In a match
Which part of the map or menu were you in? If you don't remember the exact name, please describe the area or what you were trying to do in the menu. Entire Map
What were you doing when the issue occurred? E.g. respawning a squad mate at a beacon, using an ability, a squad mate left the game. Looting Care Packages
Did your squad mates also experience the issue? I don't know
How many matches had you played in a row before the issue occurred? iv played atleast 5 matches looting atleast 2 Care packages in each
When did this happen? (dd.mm.yy hh:mm) 26/08/19
How often does the bug occur? Often (50% - 99%)
How severe is your issue? Minor impact to gameplay
What happens when the bug occurs? the daily challenge is not being completed
What should be happening instead? It should be cleared
Steps: How can we find the bug ourselves? I dont know

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So there is only 1 day left in the iron crown event and i need to complete all my daily challenges to complete the 20 daily challenge iron crown challenge

and iv been grinding on one challenge thats not clearing its the loot 2 care packages in a single match and iv done that multiple times and its counting. Iv looted 4 care packages from the map my last game and it still hasn't cleared. If this challenge doesn't clear i wont be able to complete the 20 daily challenges for the iron crown event pack.

Product: Apex Legends
Platform:PC
Please specify your platform model. PC
AMD or Nvidia Model Number Nvidia
Enter RAM memory size in GB 16GB
What is your gamertag/PSN ID/EA Account name? SilverwuIf
Please provide your squad mates' gamertag/PSN ID/EA Account name if possible.
Are you using any software with an overlay? No
Which Legend were you playing (if applicable)? Bloodhound
Which Legends were your squad mates using (if applicable)?
Where did the issue occur? Returning to the lobby after a match
Which part of the map or menu were you in? If you don't remember the exact name, please describe the area or what you were trying to do in the menu. NA
What were you doing when the issue occurred? E.g. respawning a squad mate at a beacon, using an ability, a squad mate left the game. NA
Did your squad mates also experience the issue? I don't know
How many matches had you played in a row before the issue occurred? 2ish
When did this happen? (dd.mm.yy hh:mm) 1.7.20 12:35am
How often does the bug occur? Occasionally (10% - 49%)
How severe is your issue? Minor impact to gameplay
What happens when the bug occurs? I looted 2 neutral care packages in 1 match and my challenge did not track the challenge as completed. I got nothing for completing it and it still says 0/2.
What should be happening instead? The "Loot 2 Care Packages in 1 Match" Challenge should have completed
Steps: How can we find the bug ourselves? Try looting 2 neutral care packages in 1 match from the same drop time.

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My progress is not tracking on some challenges. Specifically today I finally got to loot 2 neutral care packages in 1 match (I made sure they were not player spawned, I saw them both have drop icons on the map) and the challenge did not complete. They both dropped at the same time and I was able to loot 2 items from the first (Mastiff and extended heavy mag level 3) and then run across the map to the second to loot a Phoenix kit and I can't remember if I grabbed a second item or not.

Yesterday I was unable to get any progress on the winter challenge train captures. My squad captured the train several times (and with me alive on it) across several games and it would not track any progress. Today it started tracking progress and I was able to complete level 1 of the challenge finally.

Interesting enough I just noticed that my "Loot 5 neutral care packages" challenge says 1 care package looted. 

Product: Apex Legends
Platform:Microsoft XBOX One
Please specify your platform model. Microsoft Xbox One S
What is your gamertag/PSN ID/EA Account name? omgitsapiggy#276
Please provide your squad mates' gamertag/PSN ID/EA Account name if possible. WalkingSandwich, Harrywillo02
Are you using any software with an overlay? No
Which Legend were you playing (if applicable)? Crypto
Which Legends were your squad mates using (if applicable)? Lifeline, Bangalore
Where did the issue occur? Returning to the lobby after a match
Which part of the map or menu were you in? If you don't remember the exact name, please describe the area or what you were trying to do in the menu. Harvester
What were you doing when the issue occurred? E.g. respawning a squad mate at a beacon, using an ability, a squad mate left the game. Looting a neutral care package
Did your squad mates also experience the issue? No
How many matches had you played in a row before the issue occurred? It was fine before the the challange came out
When did this happen? (dd.mm.yy hh:mm) Don't remember the date. It was Feburary time.
How often does the bug occur? Rarely (0% - 9%)
How severe is your issue? Major impacts to gameplay
What happens when the bug occurs? I loot two neutral care packages in the game, I have done this twice now and the weekly challange does not complete itself.
What should be happening instead? Marking off my challange
Steps: How can we find the bug ourselves? As a weekly, testing the challange could be an option.

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Loot 2 neutral care packages in a single match.

I've attempted this challange twice, so far I haven't completed it but as far as I remember, I have completed this challange. It's still on my Week 2 challange and I can't complete it because it won't process my challange? 

Where do I go from here?

Same issue in may, 2020. Still happening. Can't get it to clear. Seems to be a really common issue

It is still happening. Did you ever figure out a way to register it even with this bug that everyone is experiencing in their weekly challenges?

Hello @bgunther97 and thanks for updating on this issue.

I've merged all available threads of this issue into this one, to gather all information in one place.