Could it be that your GPG passphrase is saved in the macOS keychain?
That would explain why you aren't prompted for it after a reboot.

Try opening the macOS keychain and seeing if anything comes up when you
search for "gnupg".

On 11/23/2016 01:31 PM, Cycle London wrote:
> Yes, it is encrypted.
> 
> On 23 November 2016 at 13:26, Lenz Weber <[email protected]
> <mailto:[email protected]>> wrote:
> 
>     sorry, then I interpreted your "enter password twice" wrong.
> 
>     take a look at the encrypted file
>     (~/.password-store/google.com/gmail/[email protected]
>     <http://google.com/gmail/[email protected]> ) - is it in fact
>     encrypted with gpg for that key?
> 
> 
>     On 11/23/2016 02:23 PM, Cycle London wrote:
>>     Agent *is* running, but how could that cache my passphrase, when in fact 
>> I
>>     have not entered that passphrase once, since the last time the Mac was
>>     rebooted?
>>
>>     On 23 November 2016 at 13:21, Lenz Weber <[email protected]> 
>> <mailto:[email protected]> wrote:
>>
>>>     most likely you have a gpg-agent running that caches your
>>>     passphrase? On 11/23/2016 02:16 PM, Cycle London wrote: Hello,
>>>     Trying to use 'pass' on my Mac, but it is displaying passwords
>>>     without asking for my GPG ID. I run : `pass init 0x123456789`
>>>     That gets me: Password store initialized for 0x123456789 I then
>>>     add a password to test: `pass insert
>>>     google.com/gmail/[email protected]
>>>     <mailto:google.com/gmail/[email protected]>` That gets me a
>>>     password prompt twice, so I enter the password. I then try: `[~]
>>>     john@Mac% (126) pass google.com/gmail/[email protected]
>>>     <mailto:google.com/gmail/[email protected]>` test Why doesn't it
>>>     ask for my passphrase? FYI, '0x123456789' is what I get from `gpg
>>>     --list-keys` and is the ID that comes after the key length in the
>>>     output. What am I doing wrong, or is the Mac version broken ?
>>>     Hello, Trying to use 'pass' on my Mac, but it is displaying
>>>     passwords without asking for my GPG ID. I run : `pass init
>>>     0x123456789` That gets me: Password store initialized for
>>>     0x123456789 I then add a password to test: `pass insert
>>>     google.com/gmail/[email protected]
>>>     <mailto:google.com/gmail/[email protected]>`
>>>     <http://google.com/gmail/[email protected]%60>
>>>     <http://google.com/gmail/[email protected]%60>That gets me a
>>>     password prompt twice, so I enter the password. I then try: `[~]
>>>     john@Mac% (126) pass google.com/gmail/[email protected]
>>>     <mailto:google.com/gmail/[email protected]>`
>>>     <http://google.com/gmail/[email protected]%60>
>>>     <http://google.com/gmail/[email protected]%60>
>>>     test Why doesn't it ask for my passphrase? FYI, '0x123456789' is
>>>     what I get from `gpg --list-keys` and is the ID that comes after
>>>     the key length in the output. What am I doing wrong, or is the
>>>     Mac version broken ?
>>>     _______________________________________________ Password-Store
>>>     mailing
>>>     
>>> [email protected]http://lists.zx2c4.com/mailman/listinfo/password-store
>>>     
>>> <mailto:[email protected]://lists.zx2c4.com/mailman/listinfo/password-store>
>>>
>>>
>>>
>>>     Agent *is* running, but how could that cache my passphrase, when
>>>     in fact I have not entered that passphrase once, since the last
>>>     time the Mac was rebooted?
>>>
>>>     On 23 November 2016 at 13:21, Lenz Weber <[email protected]
>>>     <mailto:[email protected]>> wrote:
>>>
>>>         most likely you have a gpg-agent running that caches your
>>>         passphrase?
>>>
>>>
>>>         On 11/23/2016 02:16 PM, Cycle London wrote:
>>>>         Hello,
>>>>         Trying to use 'pass' on my Mac, but it is displaying passwords 
>>>> without
>>>>         asking for my GPG ID.
>>>>
>>>>         I run : `pass init 0x123456789`
>>>>
>>>>         That gets me:
>>>>
>>>>         Password store initialized for 0x123456789
>>>>
>>>>         I then add a password to test:
>>>>
>>>>         `pass insert google.com/gmail/[email protected]
>>>>         <mailto:google.com/gmail/[email protected]>`
>>>>
>>>>         That gets me a password prompt twice, so I enter the password.
>>>>
>>>>         I then try:
>>>>
>>>>         `[~] john@Mac% (126) pass google.com/gmail/[email protected]
>>>>         <mailto:google.com/gmail/[email protected]>`
>>>>         test
>>>>
>>>>         Why doesn't it ask for my passphrase?
>>>>
>>>>         FYI, '0x123456789' is what I get from `gpg --list-keys` and is the 
>>>> ID that
>>>>         comes after the key length in the output.
>>>>
>>>>         What am I doing wrong, or is the Mac version broken ?
>>>>
>>>>         Hello, Trying to use 'pass' on my Mac, but it is displaying
>>>>         passwords without asking for my GPG ID. I run : `pass init
>>>>         0x123456789`
>>>>         That gets me: Password store initialized for 0x123456789
>>>>         I then add a password to test: `pass insert
>>>>         google.com/gmail/[email protected]`
>>>>         <http://google.com/gmail/[email protected]%60>
>>>>         That gets me a password prompt twice, so I enter the password. 
>>>>         I then try: `[~] john@Mac% (126) pass
>>>>         google.com/gmail/[email protected]`
>>>>         <http://google.com/gmail/[email protected]%60> test
>>>>         Why doesn't it ask for my passphrase? 
>>>>         FYI, '0x123456789' is what I get from `gpg --list-keys` and
>>>>         is the ID that comes after the key length in the output.
>>>>         What am I doing wrong, or is the Mac version broken ?
>>>>
>>>>         _______________________________________________
>>>>         Password-Store mailing list
>>>>         [email protected]
>>>>         <mailto:[email protected]>
>>>>         http://lists.zx2c4.com/mailman/listinfo/password-store
>>>>         <http://lists.zx2c4.com/mailman/listinfo/password-store>
>>>
> 
> 
> 
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