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If any transaction is pending for hours/days even after reattaching and promoting it (while connected with updated node and keep changing them for reattaching again), shall I resend it to receiver's different address?

Both of the pending transactions will try to spend from the same address of my wallet. And that will reveal 50% of the private key while they are in pending state. Right?

what should I do in this case? Keep reattaching or send again to a new address?

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You must keep promoting the pending transaction. You should also select a properly sync fullnode. (see http://iota.dance/nodes/).

As you mention yourself, sending to a different address is a double spend, it will reveal another portion of your key... and there is absolutely no guarantee that this new transaction will confirm faster.

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    Agreed. I am using iota.dance/nodes to fetch latest node info. But it means multiple parallel transactions can't be made using wallet or client as user can't choose address to spend from and it will choose same address (starting from first index)
    – Dev
    Commented Dec 20, 2017 at 9:51
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    Indeed, you can't safely have multiple pending transactions with the current wallet. But remember that iota is targeting machine-2-machine transactions where one machine can have a smart implementation of it's addresses pool (requirements depending on the service implemented by the machine)
    – ben75
    Commented Dec 20, 2017 at 9:56
  • True. Excited to see update on address pooling :)
    – Dev
    Commented Dec 20, 2017 at 9:59

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