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My Photo Stream makes it really easy for you to share your photos taken by i Phone, i Pad or i Pod touch or imported photos on your computer across all of your devices.As handy it is, you may find some issues with My Photo Stream every now and then.Photos shows but nothing happens (even after a couple of days and reboots). Is it possible your Mac is going to sleep or disconnecting from the internet at some point?
In i OS 9, I found that it comes automatically enabled.
Your image says it's still uploading and I think that needs to complete first. I have the same issue with photos going from i Phone and i Pad to i Cloud immediately, but not going to my i Mac.
I turned off Photo Library on my i Mac which prompted another 19000 photo upload which seems to be stuck at 28.32GB of some 76GB.
If you don't want to pay for the upgrade plans (up to 1T), you can look for some unlimited cloud services like Google Photos, or directly transfer the photos from i Device to local hard drive and upload photos from computer to i Cloud when mobile to mobile not syncing trouble occurs.
In reture, if your computer failed to upload photos to i Cloud, it's also feasible to sync those photos to i Phone/i Pad for smoothly syncing them to i Cloud.