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I regularly install a number of frequently used applications on new android devices.
Since I do this often, I download and the latest versions of these apps and sideload the APKs onto the devices in order to save internet bandwith among other reasons.

The problem I encounter with this is that new applications I install via sideloading do not appear in the user's application list in Google Play even though the apps are free.

How can I get these new apps added to the user's application list?

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Sideloaded apps are not linked to Google Play. You will have to update them manually (i.e. sideloading)

What you could do is install Titanium Backup (needs root), and use its Attach to Market feature.

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Another solution would be to use AppBrain instead of Google Play, because AppBrain scans the apps in your phone, and informs you of any updates.

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