diff --git a/app/Http/Controllers/Api/V1/MemberController.php b/app/Http/Controllers/Api/V1/MemberController.php
index 9a8e8876..484a02f5 100644
--- a/app/Http/Controllers/Api/V1/MemberController.php
+++ b/app/Http/Controllers/Api/V1/MemberController.php
@@ -16,6 +16,7 @@ use App\Exceptions\Api\OrganizationNeedsAtLeastOneOwner;
 use App\Exceptions\Api\ThisPlaceholderCanNotBeInvitedUseTheMergeToolInsteadException;
 use App\Exceptions\Api\UserIsAlreadyMemberOfOrganizationApiException;
 use App\Exceptions\Api\UserNotPlaceholderApiException;
+use App\Http\Requests\V1\Member\MemberDestroyRequest;
 use App\Http\Requests\V1\Member\MemberIndexRequest;
 use App\Http\Requests\V1\Member\MemberMergeIntoRequest;
 use App\Http\Requests\V1\Member\MemberUpdateRequest;
@@ -100,11 +101,13 @@ class MemberController extends Controller
      *
      * @operationId removeMember
      */
-    public function destroy(Organization $organization, Member $member, MemberService $memberService): JsonResponse
+    public function destroy(MemberDestroyRequest $request, Organization $organization, Member $member, MemberService $memberService): JsonResponse
     {
         $this->checkPermission($organization, 'members:delete', $member);
 
-        $memberService->removeMember($member, $organization);
+        $deleteRelated = $request->getDeleteRelated();
+
+        $memberService->removeMember($member, $organization, $deleteRelated);
 
         return response()
             ->json(null, 204);
diff --git a/app/Http/Requests/V1/Member/MemberDestroyRequest.php b/app/Http/Requests/V1/Member/MemberDestroyRequest.php
new file mode 100644
index 00000000..18231496
--- /dev/null
+++ b/app/Http/Requests/V1/Member/MemberDestroyRequest.php
@@ -0,0 +1,35 @@
+<?php
+
+declare(strict_types=1);
+
+namespace App\Http\Requests\V1\Member;
+
+use App\Http\Requests\V1\BaseFormRequest;
+use App\Models\Organization;
+use Illuminate\Contracts\Validation\ValidationRule;
+
+/**
+ * @property Organization $organization
+ */
+class MemberDestroyRequest extends BaseFormRequest
+{
+    /**
+     * Get the validation rules that apply to the request.
+     *
+     * @return array<string, array<string|ValidationRule>>
+     */
+    public function rules(): array
+    {
+        return [
+            'delete_related' => [
+                'string',
+                'in:true,false',
+            ],
+        ];
+    }
+
+    public function getDeleteRelated(): bool
+    {
+        return $this->input('delete_related', 'false') === 'true';
+    }
+}
diff --git a/app/Service/MemberService.php b/app/Service/MemberService.php
index d88660f7..3a45a12a 100644
--- a/app/Service/MemberService.php
+++ b/app/Service/MemberService.php
@@ -61,18 +61,24 @@ class MemberService
      * @throws CanNotRemoveOwnerFromOrganization
      * @throws EntityStillInUseApiException
      */
-    public function removeMember(Member $member, Organization $organization): void
+    public function removeMember(Member $member, Organization $organization, bool $withRelations = false): void
     {
-        if (TimeEntry::query()->where('user_id', $member->user_id)->whereBelongsTo($organization, 'organization')->exists()) {
-            throw new EntityStillInUseApiException('member', 'time_entry');
-        }
-        if (ProjectMember::query()->whereBelongsToOrganization($organization)->where('user_id', $member->user_id)->exists()) {
-            throw new EntityStillInUseApiException('member', 'project_member');
-        }
         if ($member->role === Role::Owner->value) {
             throw new CanNotRemoveOwnerFromOrganization;
         }
 
+        if ($withRelations) {
+            TimeEntry::query()->where('user_id', $member->user_id)->whereBelongsTo($organization, 'organization')->delete();
+            ProjectMember::query()->whereBelongsToOrganization($organization)->where('user_id', $member->user_id)->delete();
+        } else {
+            if (TimeEntry::query()->where('user_id', $member->user_id)->whereBelongsTo($organization, 'organization')->exists()) {
+                throw new EntityStillInUseApiException('member', 'time_entry');
+            }
+            if (ProjectMember::query()->whereBelongsToOrganization($organization)->where('user_id', $member->user_id)->exists()) {
+                throw new EntityStillInUseApiException('member', 'project_member');
+            }
+        }
+
         $member->delete();
         MemberRemoved::dispatch($member, $organization);
     }
diff --git a/tests/Unit/Endpoint/Api/V1/MemberEndpointTest.php b/tests/Unit/Endpoint/Api/V1/MemberEndpointTest.php
index 011702af..dd157d6c 100644
--- a/tests/Unit/Endpoint/Api/V1/MemberEndpointTest.php
+++ b/tests/Unit/Endpoint/Api/V1/MemberEndpointTest.php
@@ -653,6 +653,85 @@ class MemberEndpointTest extends ApiEndpointTestAbstract
         Event::assertNotDispatched(MemberRemoved::class);
     }
 
+    public function test_destroy_endpoint_succeeds_if_member_is_still_in_use_by_a_project_member_and_delete_related_is_active(): void
+    {
+        // Arrange
+        $data = $this->createUserWithPermission([
+            'members:delete',
+        ]);
+        $otherMember = Member::factory()->forOrganization($data->organization)->role(Role::Employee)->create();
+        $project = Project::factory()->forOrganization($data->organization)->create();
+        $projectMember = ProjectMember::factory()->forProject($project)->forMember($data->member)->create();
+        $otherProjectMember = ProjectMember::factory()->forProject($project)->forMember($otherMember)->create();
+        Passport::actingAs($data->user);
+        Event::fake([
+            MemberRemoved::class,
+        ]);
+
+        // Act
+        $response = $this->deleteJson(route('api.v1.members.destroy', [
+            'organization' => $data->organization->getKey(),
+            'member' => $data->member->getKey(),
+            'delete_related' => 'true',
+        ]));
+
+        // Assert
+        $response->assertStatus(204);
+        $this->assertDatabaseMissing(Member::class, [
+            'id' => $data->member->getKey(),
+        ]);
+        $this->assertDatabaseHas(ProjectMember::class, [
+            'id' => $otherProjectMember->getKey(),
+            'member_id' => $otherMember->getKey(),
+            'user_id' => $otherMember->user_id,
+        ]);
+        $this->assertDatabaseMissing(ProjectMember::class, [
+            'id' => $projectMember->getKey(),
+        ]);
+        Event::assertDispatched(function (MemberRemoved $event) use ($data): bool {
+            return $event->organization->is($data->organization) &&
+                $event->member->is($data->member);
+        }, 1);
+    }
+
+    public function test_destroy_endpoint_succeeds_if_member_is_still_in_use_by_a_time_entry_and_delete_related_is_active(): void
+    {
+        // Arrange
+        $data = $this->createUserWithPermission([
+            'members:delete',
+        ]);
+        $otherMember = Member::factory()->forOrganization($data->organization)->role(Role::Employee)->create();
+        $timeEntry = TimeEntry::factory()->forMember($data->member)->forOrganization($data->organization)->create();
+        $otherTimeEntry = TimeEntry::factory()->forMember($otherMember)->forOrganization($data->organization)->create();
+        Passport::actingAs($data->user);
+        Event::fake([
+            MemberRemoved::class,
+        ]);
+
+        // Act
+        $response = $this->deleteJson(route('api.v1.members.destroy', [
+            'organization' => $data->organization->getKey(),
+            'member' => $data->member->getKey(),
+            'delete_related' => 'true',
+        ]));
+
+        // Assert
+        $response->assertStatus(204);
+        $this->assertDatabaseMissing(Member::class, [
+            'id' => $data->member->getKey(),
+        ]);
+        $this->assertDatabaseHas(TimeEntry::class, [
+            'id' => $otherTimeEntry->getKey(),
+        ]);
+        $this->assertDatabaseMissing(TimeEntry::class, [
+            'id' => $timeEntry->getKey(),
+        ]);
+        Event::assertDispatched(function (MemberRemoved $event) use ($data): bool {
+            return $event->organization->is($data->organization) &&
+                $event->member->is($data->member);
+        }, 1);
+    }
+
     public function test_destroy_member_succeeds_if_data_is_valid(): void
     {
         // Arrange