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Sometimes an SMS fails to send but I would not notice it as I already put the phone in my pocket?

How do I set Android to automatically retry sending failed SMS?

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unfortunately this isn't an option on the stock android ROM's, regardless of the version. After doing a little research, it seems that if you wish to root your phone and install a new ROM that the Desire flavor of ROM's (I don't know if it is available for your model of phone since you didn't specify the model) has this feature built into the ROM itself.

After some more research (this was harder to find than I expected) there is an app that has built in auto-retry of failed sms messages. Please see This XDA Forum Post for details about it. It is a replacement messaging client for your android phone which includes this feature.

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