How can I force Photos to update "My Photo Stream"?
My Photo Stream in Photos on my iMac is rarely up to date when compared with my iPhone. How can I force it to update itself?
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There is nothing you can do to force it.
Has your phone recently updated? Is it taking pictures in HEIC format? Recent releases of IOS have stopped converting HEIC to JPG for photostream, and since photostream won't transfer HEIC, you don't get them.
If this is the case here, you need to set the format (on your phone camera settings) to "most compatible" If you do this though, your photos will take approximately twice as much space from then on.