diff --git a/src/Api/AdminConsole/Controllers/OrganizationsController.cs b/src/Api/AdminConsole/Controllers/OrganizationsController.cs
index 0b3811618..e134adc04 100644
--- a/src/Api/AdminConsole/Controllers/OrganizationsController.cs
+++ b/src/Api/AdminConsole/Controllers/OrganizationsController.cs
@@ -252,6 +252,12 @@ public class OrganizationsController : Controller
             throw new BadRequestException("Your organization's Single Sign-On settings prevent you from leaving.");
         }
 
+        if (_featureService.IsEnabled(FeatureFlagKeys.AccountDeprovisioning)
+            && (await _userService.GetOrganizationsManagingUserAsync(user.Id)).Any(x => x.Id == id))
+        {
+            throw new BadRequestException("Managed user account cannot leave managing organization. Contact your organization administrator for additional details.");
+        }
+
         await _removeOrganizationUserCommand.RemoveUserAsync(id, user.Id);
     }
 
diff --git a/test/Api.Test/AdminConsole/Controllers/OrganizationsControllerTests.cs b/test/Api.Test/AdminConsole/Controllers/OrganizationsControllerTests.cs
index 25227fec7..13826888d 100644
--- a/test/Api.Test/AdminConsole/Controllers/OrganizationsControllerTests.cs
+++ b/test/Api.Test/AdminConsole/Controllers/OrganizationsControllerTests.cs
@@ -51,7 +51,6 @@ public class OrganizationsControllerTests : IDisposable
     private readonly IProviderBillingService _providerBillingService;
     private readonly IDataProtectorTokenFactory<OrgDeleteTokenable> _orgDeleteTokenDataFactory;
     private readonly IRemoveOrganizationUserCommand _removeOrganizationUserCommand;
-
     private readonly OrganizationsController _sut;
 
     public OrganizationsControllerTests()
@@ -123,7 +122,8 @@ public class OrganizationsControllerTests : IDisposable
         _currentContext.OrganizationUser(orgId).Returns(true);
         _ssoConfigRepository.GetByOrganizationIdAsync(orgId).Returns(ssoConfig);
         _userService.GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).Returns(user);
-
+        _featureService.IsEnabled(FeatureFlagKeys.AccountDeprovisioning).Returns(true);
+        _userService.GetOrganizationsManagingUserAsync(user.Id).Returns(new List<Organization> { null });
         var exception = await Assert.ThrowsAsync<BadRequestException>(() => _sut.Leave(orgId));
 
         Assert.Contains("Your organization's Single Sign-On settings prevent you from leaving.",
@@ -132,6 +132,36 @@ public class OrganizationsControllerTests : IDisposable
         await _removeOrganizationUserCommand.DidNotReceiveWithAnyArgs().RemoveUserAsync(default, default);
     }
 
+    [Theory, AutoData]
+    public async Task OrganizationsController_UserCannotLeaveOrganizationThatManagesUser(
+        Guid orgId, User user)
+    {
+        var ssoConfig = new SsoConfig
+        {
+            Id = default,
+            Data = new SsoConfigurationData
+            {
+                MemberDecryptionType = MemberDecryptionType.KeyConnector
+            }.Serialize(),
+            Enabled = true,
+            OrganizationId = orgId,
+        };
+        var foundOrg = new Organization();
+        foundOrg.Id = orgId;
+
+        _currentContext.OrganizationUser(orgId).Returns(true);
+        _ssoConfigRepository.GetByOrganizationIdAsync(orgId).Returns(ssoConfig);
+        _userService.GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).Returns(user);
+        _featureService.IsEnabled(FeatureFlagKeys.AccountDeprovisioning).Returns(true);
+        _userService.GetOrganizationsManagingUserAsync(user.Id).Returns(new List<Organization> { { foundOrg } });
+        var exception = await Assert.ThrowsAsync<BadRequestException>(() => _sut.Leave(orgId));
+
+        Assert.Contains("Managed user account cannot leave managing organization. Contact your organization administrator for additional details.",
+            exception.Message);
+
+        await _removeOrganizationUserCommand.DidNotReceiveWithAnyArgs().RemoveUserAsync(default, default);
+    }
+
     [Theory]
     [InlineAutoData(true, false)]
     [InlineAutoData(false, true)]
@@ -157,6 +187,8 @@ public class OrganizationsControllerTests : IDisposable
         _currentContext.OrganizationUser(orgId).Returns(true);
         _ssoConfigRepository.GetByOrganizationIdAsync(orgId).Returns(ssoConfig);
         _userService.GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).Returns(user);
+        _featureService.IsEnabled(FeatureFlagKeys.AccountDeprovisioning).Returns(true);
+        _userService.GetOrganizationsManagingUserAsync(user.Id).Returns(new List<Organization>());
 
         await _sut.Leave(orgId);