Antonio,

could you describe in more detail what the issue looks like containing detailed 
steps of what you expect and what the actual outcome is. For a step-by-step on 
how to proceed have a look at (you can just copy paste it):
* https://github.com/GPGTools/GPGMail/wiki/Found-an-issue

Further could you attach an error-log from when this happens.

Hope we can track down this odd behavior.

Cheers,
Steve

@Alex did we have a testing script, maybe you could post a link? (Can't find it 
right now).


> Dear All,
> 
> Once again I come seeking your assistance...
> 
> There is one particular email address to where I send messages that GPGMail 
> is no longer requesting me to type my Passphrase. I've not change any of the 
> settings that would cause that to happen.
> All the other emails addresses require me to type the Passphrase, even if 
> I've previously sent email to it. 
> What should I do? Is there a way for a total reset of the system in order to 
> solve this issue?
> Thank you and best regards,
> 
> Antonio Gantus Filho
> 
> "This message is intended only for the named person's and/or entity's use and 
> may contain confidential, proprietary or legally privileged information, 
> which shall not be used, disclosed, changed, printed or copied, in whole or 
> in part, by not intended recipients. If this message is received by error, 
> please delete it from your system and/or destroy any hard copies of it and 
> notify the sender, immediately. No confidentiality or privilege is waived by 
> any mistransmission."
> 
> 
> 
> 
> 
> -----BEGIN PGP SIGNATURE-----
> Version: GnuPG/MacGPG2 v2.0.17 (Darwin)
> Comment: GPGTools - http://gpgtools.org
> 
> iQIcBAEBAgAGBQJNmt5sAAoJEBvIqKHn/R5FDfsQAJuEXgaVTrhYDd5iuTzEFDiZ
> 179Gq5gzgnjk8Zrjps/G36W72sA1OMdtyq/Uw7LtyWX9Ca5q946SSQlF9L3DmHtn
> HYA7dGwAi+hEBz4myqgodjwSZ1D6Fbpb8ibbXV0wKgvbodq5B9dfvbg9vxUZBCbH
> S8eM3zzhV2/g7cWhrJzJbBc9gI4OQ2y5p7HcsLkCKDsVdZsO4a7Rc0ibg7fVgeii
> RNa6FS+nBlYK3XhL0uE+QVPUSGr2M1IXpHNmfT50ttpNReXTvBqtMliJeDZyOwGN
> vh1IIqM/2mO7u2SnfvP+4IttN6Sr1zGZQQVZdh3L2sD4pHJYM3yTCJfRHRC8i6iT
> cVCcouDHBnQEO712Ba+GSGaGbetjMS3JkrkxRvUDAwiwC84y4P/4+XDi2hokL4PJ
> Z5GrRlEzMWwYHq/q0MbkgZd5TdZUwkjln7s9iX148uflMTo9GuJvDgm4IqqwqAHg
> Xtf/3Mw+5cU/PLaGCxyhv0qqm6xPF4oS61I/cue5q+axQ8hwLQi43K+zvo5WiTpO
> cu1uAeDH67eUerS5GpFuFQ7Hh9BBam7CfQwGy54SyLnCo1m9iim07ByU3UY3SUM0
> pZPFfQlRm+aJzsrpKyGz/2ssL3GDy4vETDQPxnzlOHOXYxBFgJYqngLsHHr19jl9
> 7aRdYNTKHscUQupKZmpF
> =gcfg
> -----END PGP SIGNATURE-----
> 
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