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    OS X Keychain Issue: Frequent Prompts to Allow Access to Keychain Items

    When using the OS X keychain, sometimes after an upgrade of 1Password you are required to allow access to each of its items. You may see a prompt like this one:

    OS X Security Agent Prompt

    There are a few causes of this problem, but the end result is that you need to click Always Allow for every single item stored in your OS X keychain.

    The Problem: Leopard + Firewall + iPhone Sync

    While there are other causes, the primary cause of this problem is related to how Leopard handles Wi-Fi syncing with the iPhone/iPod touch application, specifically when firewalls are enabled.

    On Leopard systems that have the firewall enabled, Wi-Fi syncing will cause Leopard to implicitly codesign the 1Password application. Once implicitly signed, the keychain treats 1Password as a completely new application and proceeds to prompt you for confirmation on every single item in the keychain. Worst of all, after any update, Leopard will re-sign 1Password, causing the cycle to repeat itself.

    The Solution

    Unfortunately there is no easy way around these prompts. You will need to click Always Allow for every single item. If you position your mouse over the Always Allow button and then quickly click the button, you will be able to complete this tedious process in a relatively short period of time.

    Once completed, upgrade to the Agile keychain format to prevent this from ever happening again. The new Agile keychain offers many benefits, one of the most enticing of which is avoiding this problem entirely.


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