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I removed the ability to login as another user from one from my custom roles. But now i want to give back the ability to do so and can't remember where the setting is at. Anyone wanna take a swing at what option i need to click back on?

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I believe this is the doc you are looking for here:

Delegate User Administration | Salesforce
Delegate User Administration Enable delegated administrators to manage users in specified roles and all subordinate roles, assign specified profiles to those users, and log in as users who have granted login access to administrators. Available in: Enterprise, Performance, Unlimited, Developer, and Database.com Editions

User Permissions Needed To manage delegated administration: “Customize Application” To be a delegated administrator: “View Setup and Configuration” From Setup, click Security Controls | Delegated Administration. Select the name of an existing delegated administration group. Click Add in the User Administration related list. Use the magnifying glass lookup icon to find and add roles. Delegated administrators can create and edit users in these roles and all subordinated roles. Click Save. Click Add in the Assignable Profiles related list. Use the magnifying glass lookup icon to find and add profiles. Delegated administrators can assign these profiles to the users they create and edit.
Note:
- Delegated administrators can’t assign profiles with the “Modify All

  • Data” permission. Delegated administrators who are members of multiple delegated administration groups can assign any assignable
    profiles to any of the users in roles that they can manage.

Click Save.

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Turns out that i forgot to check the Modify All Data option on the user profile.

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