I’m having a problem too, and I run Zwift on my iPad. For me, the problem started Sunday, November 1st. No problems on October 31st getting Zwift to save images I took in-game, but yesterday and today none of the pictures I took while Zwifting saved. I was able to save pictures taken using Companion, but using Companion (on my phone) for pics using my setup was definitely a bit of a challenge.
yep same for me on windows 10, when I save the game closes much faster than before, ignoring the photos iv saved 
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The problem still persists (Mac OS, fresh Zwift install).
Today it didn’t upload any of the 3 selected images. The other day it uploaded one of three. Here’s the snippet from that log file with 1/3 success rate:
[17:52:20] Uploading /Users/user/Pictures/Zwift/2020-11-01_1726581.jpg...
[17:52:20] NETCLIENT:[INFO] Activity Image Upload: load image file from path /Users/user/Pictures/Zwift/2020-11-01_1726581.jpg
[17:52:20] NETCLIENT:[INFO] Activity Upload: image file is length 1150776
[17:52:20] Starting critical power curve search job (12550846) mTimeStamp = 3947.28882 m_lastSearchTime = 3947.28882 calculating=false
[17:52:21] FPS 29, -106285, 26148, 104064
[17:52:22] .../Users/user/Pictures/Zwift/2020-11-01_1726581.jpg uploaded!
[17:52:22] Unable to upload ! File not found!
[17:52:22] Unknown power data [19] [128] [0] [255] [0] [255] [255] [255]
[17:52:22] Registered segment 81 with hash id 1497816
[17:52:22] ANT : Rx Fail on channel 1
[17:52:22] Unable to upload ! File not found!
[17:52:22] Done uploading screenshots.
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I’m experiencing the same issue (on Mac). Only the “F10 screenshots” fail to upload, “Automatic taken screenshots” are uploading normally. Reading the LOG file I can see the same “Unable to upload ! File not found!” message.
Is it something as simple as the code has an incorrect reference - is the user in the folder supposed to be a variable name, eg “…/Users/$user/Pictures/Zwift/” which would get expanded out to “…/Users/fred/Pictures/Zwift/” ?
Edit: odd though that the file is found at first to get the size
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From a log file where the image upload did work (a week or so ago):
[7:11:31] NETCLIENT:[INFO] Activity Image Upload: load image file from path C:\Users\david\Pictures\Zwift/2020-10-28_0600451.jpg
[7:11:31] NETCLIENT:[INFO] Activity Upload: image file is length 521173
(more stuff)
[7:11:31] …C:\Users\david\Pictures\Zwift/2020-10-28_0600451.jpg uploaded!
[7:11:31] Done uploading screenshots.
David, I intentionally replaced my real username with a “placeholder” so template substitution is unlikely to be a root cause. The path for the first file is correct and the file was successfully uploaded.
The log however does not contain the path to the “missing” file for which I had
Unable to upload ! File not found!
(who might have thought this information could be useful 
)
That makes sense then!
I think I have found the answer… since apple introduced tighter security features on its last major update- this included restricted app access to photos unless you give new permission to access you photos for your apps- I found as soon as I tried using the zwift companion app- on my phone, took photos, then when the ride started to upload, zwift asked for permission to access or manage photos- giving access to all photos fixed the issue for me 
Yay!
Hopefully this helps others with photo uploads 
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Now do Windows. 
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No pictures uploaded for me since October 26th on Windows 10 using f10
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Two weeks down, still no acknowledgement that there’s even a problem. Guess we’re waiting until the next update at the earliest.
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Still broken.
How tangled is the game’s code that features that have worked for years suddenly break? It’s ridiculous.
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Gonna be a lot of unhappy people today when they find their Fondo screenshots aren’t saved to their feed.
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Thanks, an entire year since I joined the forum without meaning to. 
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Tried reinstalling zwift, didn’t help
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Today, one of the two images I had taken and selected did appear on my Strava feed and activity in Companion.
also broken for me. annoying that features keep breaking. my withings scales still won’t sync, zwift broke the function months ago, acknowledge it, but haven’t fixed it yet.