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When you deploy iOS app to the device, delete the application on the device or plug in a new device, pressing "Run" will not deploy the application to the device. If you then click Run -> Upload to Device, it will work but it should work through just the "Run" button.
We can solve the multi-device issue by storing the device UUID in the monotouch_uploaded marker file when the upload occurs and comparing the current uuid with the stored one with the current one when deciding if an upload is required. However there is no easy way to detect if the app is installed or not when the uuid is the same, so I won't even attempt to cover that case yet.
This has been fixed