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when I receive an encrypted email from one specific person, in both my enigmail setups on different computers, the normal "Please enter the OpenPGP secret passphrase" window repeatedly pops up - for every secret identity (e.g. email adress) i have set up on the respective computer (different numbers on both computers).

This is really strange since the email is only send to one of these identities. After closing every single window that pops up (around 10-20 times) the message is, as expected, decrypted because I typed in the correct passphrase for the mail adress that it has been written to. Once I switch to another email and back the problem occures again. Its really frustrating.

I use Enigmail 1.9.4 with gpg 2.0.28 using libgcrypt 1.6.3. The ubuntu version is 14.04 on the one and 15.10 on the other machine.

Any hint is greatly appreciated. Thanks!

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Very likely, the sender chose not to include the recipient's (yours) key as reference in the encrypted message. This results in extended privacy (as the encryption headers do not leak the recipient), but increases the hassles for the recipient. GnuPG can only derive the proper key by trying all of them.

For e-mail, this does not seem to be a reasonable thing to me for normal use cases: the recipient is listed in the message envelope and headers, anyway. Tell the sender not to be over-cautious, especially when there is no advantage in privacy at all.

You can verify by running gpg --list-packets on the message to see whether the recipient is included or not (might get a little bit more difficult for PGP/MIME encrypted mails):

$ echo foo | gpg --hidden-recipient a4ff2279 --encrypt | gpg --batch --list-packets
:pubkey enc packet: version 3, algo 1, keyid 0000000000000000
    data: [4091 bits]
[ a lot of "trying secret key" messages follow ]
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