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What's the difference between this and CloudApp set to "auto upload screenshot" ?

This is a genuine question. Am I missing something here?

CloudAPp doesn't allow you to annotate the screenshots though.

But it has robust backend infrastructure and it has been around for a while.

You know... trivial extra feature vs. maturity and reliability... it's not a hard choice. Besides there are CloudApp clients that support annotations if that's what someone really needs.

Also, You can install plugins, called "raindrops" to add a few neat features, or make your own plugins since they have a raindrops API.

And the free package covers almost everything that 'Glui' does, for free.

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