Q: I recently upgraded to iOS 5 and am loving the Photo Stream capability with one exception: I can’t figure out how to batch delete photos from the Camera Roll—whether it be on the iPhone itself or in iPhoto—after choosing the ones I like in iPhoto. I enjoy taking as many pictures as possible and then weeding out the ones I don’t like later. Will I be forced to either individually delete every photo or will I have to carry around everything I ever shoot?
– Jordon

A: Unfortunately, there is no way to automatically batch delete photos that have been uploaded to Photo Stream directly on your iOS device—for that you’re basically stuck deleting photos manually, although you can select multiple photos and delete them in a single step simply by going into the Photos app on your iPhone and tapping the edit button in the top-right corner of the thumbnail view. You’ll still have to tap each one manually to select it and then tap the “Delete” button at the bottom of the screen, but this is still a bit faster than going through and deleting them one-by-one.
iPhoto and Aperture actually can be used to automatically remove photos from your Camera Roll that have been imported via the Photo Stream feature, however this requires that you connect your iPhone to your computer via USB and select it in the appropriate application as if you were importing photos manually.
Note that if you’re recording video on your iPhone, you’ll need to plug it in to transfer your videos anyway as these aren’t supported by Photo Stream.
When you connect your iPhone or other iOS device to your computer and select it in iPhoto, you will be shown a list of items that have already been imported into your library, including those pictures that have already been transferred in via Photo Stream. Items that are on your device but not in your iPhoto library will be shown below and the main “Import” button will only import those items.
However, if all of the items on your device are already in your iPhoto library, you will instead see a note to this effect with a button that can be used to remove all of those items from your device’s Camera Roll.
Note that for this to work you must actually be importing your photos into iPhoto, either automatically or manually, and these photos must still exist in your iPhoto library when you connect your iPhone.
Photos that are simply displayed in the Photo Stream section in iPhoto are not considered part of your actual iPhoto library and will not be detected when comparing your iPhoto library to your iPhone Camera Roll. This also means that if you’re using the main “Photo Stream” section to select photos for importing manually, any photos that you choose not to import will still be detected as new items from your iPhone, as these are not actually in your library.
A better way to handle this is to simply set iPhoto to import everything from your Photo Stream into your library. This option can be enabled in your iPhoto Photo Stream settings.
This will automatically create an iPhoto Event for each month of content in your Photo Stream, placing the appropriate content into each event by month.