tag:gpgtools.tenderapp.com,2011-11-04:/discussions/problems/77360-gpg-keychain-gpgservices-pinentry-mac-keeps-asking-for-passphraseGPGTools: Discussion 2018-11-17T18:29:04Ztag:gpgtools.tenderapp.com,2011-11-04:Comment/457677212018-07-25T15:54:22Z2018-07-25T15:54:22ZGPG Keychain: GPGServices: Pinentry Mac keeps asking for passphrase<div><p>Hi Scott,</p>
<p>welcome to the GPGTools support platform. Sorry you are having problems using GPG Suite.</p>
<p>Please see this <a href="https://gpgtools.tenderapp.com/kb/faq/passphrase-management">KB-article</a> on how to manage passwords for your keys.</p>
<p>Do you have the option to store your password in macOS keychain enabled?</p>
<p>When pinentry shows up, do you see the corresponding checkbox ticked?</p>
<p>When you send yourself a test message which is encrypted and signed and enter your password with the checkbox enabled and then send another test email, are you then still asked for your password?</p>
<p>Best,<br>
steve</p></div>Stevetag:gpgtools.tenderapp.com,2011-11-04:Comment/457677212018-07-25T16:18:37Z2018-07-25T16:18:39ZGPG Keychain: GPGServices: Pinentry Mac keeps asking for passphrase<div><p>Greetings,</p>
<p>Thanks so much for your support!</p>
<p>Do you have the option to store your password in macOS keychain enabled?<br>
*Yes I have that box checked (it has been, no changes recently, this just started happening)</p>
<p>When pinentry shows up, do you see the corresponding checkbox ticked?<br>
*Yes and it is checked by default on that pop up window, which is why I find it odd keeps popping up</p>
<p>When you send yourself a test message which is encrypted and signed<br>
and enter your password with the checkbox enabled and then send<br>
another test email, are you then still asked for your password?<br>
*I just sent test message, it did not prompt me for password. Maybe the behavior I"m seeing is random / not every time.</p>
<p>I rebooted couple of times since this trouble, and checks for updates<br>
on GPG suite (says current = 2018.3)</p>
<p>Next time it pops up I'll catch screen shot of it and share!</p>
<p>Cheers,</p>
<p>Scott</p></div>Scott Jonestag:gpgtools.tenderapp.com,2011-11-04:Comment/457677212018-07-26T10:50:05Z2018-07-26T10:50:05ZGPG Keychain: GPGServices: Pinentry Mac keeps asking for passphrase<div><p>Thanks for the detailed reply.</p>
<p>This sounds odd indeed. Note that the transition from MacGPG 2.0.x to 2.2.x requires users to re-enter their password for their OpenPGP key. And depending on the key, you may be asked twice (once for signing, once for decrypting). So far the requests would be expected.</p>
<p>The fact that things are now working as expected is good news.</p>
<p>Please do as you already wrote: closely observe the behavior and let us know if you are asked again and in that case please create a screenshot of the request.</p>
<p>Best,<br>
steve</p></div>Stevetag:gpgtools.tenderapp.com,2011-11-04:Comment/457677212018-07-26T15:38:57Z2018-07-26T15:38:58ZGPG Keychain: GPGServices: Pinentry Mac keeps asking for passphrase<div><p>Greetings Steve,</p>
<p>Thanks again for the great support!</p>
<p>For more testing, I un-checked to cache, then re-checked to cache<br>
(Perhaps to toggle the process responsible or caching this OFF then back ON). Rebooted, and so far I have not been repeatedly promoted<br>
for password today.</p>
<p>Going to work throughout the day (lots of email) and let you know how it goes!!</p>
<p>Cheers,</p>
<p>Scott</p></div>Scott Jonestag:gpgtools.tenderapp.com,2011-11-04:Comment/457677212018-07-29T11:13:00Z2018-07-29T11:13:00ZGPG Keychain: GPGServices: Pinentry Mac keeps asking for passphrase<div><p>Hey Scott,</p>
<p>that sounds like good news. Is your setup now working as expected?</p>
<p>Best,<br>
steve</p></div>Stevetag:gpgtools.tenderapp.com,2011-11-04:Comment/457677212018-07-30T01:41:26Z2018-07-30T01:41:27ZGPG Keychain: GPGServices: Pinentry Mac keeps asking for passphrase<div><p>Hi Steve,</p>
<p>So far no more pop up, but I've been on PTO, going to send lots of<br>
email tomorrow will let you know!</p>
<p>Thanks!</p>
<p>Scott</p></div>Scott Jones