diff --git a/authentik/sources/ldap/api.py b/authentik/sources/ldap/api.py
index 16741caa3ed3..bb04682afad7 100644
--- a/authentik/sources/ldap/api.py
+++ b/authentik/sources/ldap/api.py
@@ -99,6 +99,7 @@ class Meta:
             "sync_groups",
             "sync_parent_group",
             "connectivity",
+            "lookup_groups_from_user",
         ]
         extra_kwargs = {"bind_password": {"write_only": True}}
 
@@ -134,6 +135,7 @@ class LDAPSourceViewSet(UsedByMixin, ModelViewSet):
         "sync_parent_group",
         "user_property_mappings",
         "group_property_mappings",
+        "lookup_groups_from_user",
     ]
     search_fields = ["name", "slug"]
     ordering = ["name"]
diff --git a/authentik/sources/ldap/migrations/0007_ldapsource_lookup_groups_from_user.py b/authentik/sources/ldap/migrations/0007_ldapsource_lookup_groups_from_user.py
new file mode 100644
index 000000000000..d2cfce45d686
--- /dev/null
+++ b/authentik/sources/ldap/migrations/0007_ldapsource_lookup_groups_from_user.py
@@ -0,0 +1,24 @@
+# Generated by Django 4.1.2 on 2022-10-31 16:30
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        (
+            "authentik_sources_ldap",
+            "0006_rename_ldappropertymapping_ldapsourcepropertymapping_and_more",
+        ),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name="ldapsource",
+            name="lookup_groups_from_user",
+            field=models.BooleanField(
+                default=False,
+                help_text="Lookup group membership based on a user attribute instead of a group attribute.This allows nested group resolution on systems like FreeIPA",
+            ),
+        ),
+    ]
diff --git a/authentik/sources/ldap/models.py b/authentik/sources/ldap/models.py
index dcfa0ccc1ecd..4fe046dfd1aa 100644
--- a/authentik/sources/ldap/models.py
+++ b/authentik/sources/ldap/models.py
@@ -123,6 +123,14 @@ class LDAPSource(Source):
         Group, blank=True, null=True, default=None, on_delete=models.SET_DEFAULT
     )
 
+    lookup_groups_from_user = models.BooleanField(
+        default=False,
+        help_text=_(
+            "Lookup group membership based on a user attribute instead of a group attribute."
+            "This allows nested group resolution on systems like FreeIPA and Active Directory"
+        ),
+    )
+
     @property
     def component(self) -> str:
         return "ak-source-ldap-form"
diff --git a/authentik/sources/ldap/sync/membership.py b/authentik/sources/ldap/sync/membership.py
index 853e98fdc6e6..cbeaacbdd1c6 100644
--- a/authentik/sources/ldap/sync/membership.py
+++ b/authentik/sources/ldap/sync/membership.py
@@ -28,15 +28,17 @@ def get_objects(self, **kwargs) -> Generator:
         if not self._source.sync_groups:
             self.message("Group syncing is disabled for this Source")
             return iter(())
+
+        # If we are looking up groups from users, we don't need to fetch the group membership field
+        attributes = [self._source.object_uniqueness_field, LDAP_DISTINGUISHED_NAME]
+        if not self._source.lookup_groups_from_user:
+            attributes.append(self._source.group_membership_field)
+
         return self.search_paginator(
             search_base=self.base_dn_groups,
             search_filter=self._source.group_object_filter,
             search_scope=SUBTREE,
-            attributes=[
-                self._source.group_membership_field,
-                self._source.object_uniqueness_field,
-                LDAP_DISTINGUISHED_NAME,
-            ],
+            attributes=attributes,
             **kwargs,
         )
 
@@ -47,9 +49,24 @@ def sync(self, page_data: list) -> int:
             return -1
         membership_count = 0
         for group in page_data:
-            if "attributes" not in group:
-                continue
-            members = group.get("attributes", {}).get(self._source.group_membership_field, [])
+            if self._source.lookup_groups_from_user:
+                group_dn = group.get("dn", {})
+                group_filter = f"({self._source.group_membership_field}={group_dn})"
+                group_members = self._source.connection().extend.standard.paged_search(
+                    search_base=self.base_dn_users,
+                    search_filter=group_filter,
+                    search_scope=SUBTREE,
+                    attributes=[self._source.object_uniqueness_field],
+                )
+                members = []
+                for group_member in group_members:
+                    group_member_dn = group_member.get("dn", {})
+                    members.append(group_member_dn)
+            else:
+                if "attributes" not in group:
+                    continue
+                members = group.get("attributes", {}).get(self._source.group_membership_field, [])
+
             ak_group = self.get_group(group)
             if not ak_group:
                 continue
@@ -68,7 +85,7 @@ def sync(self, page_data: list) -> int:
                         "ak_groups__in": [ak_group],
                     }
                 )
-            )
+            ).distinct()
             membership_count += 1
             membership_count += users.count()
             ak_group.users.set(users)
diff --git a/blueprints/schema.json b/blueprints/schema.json
index 8fd4002d447e..9a6fd52333f1 100644
--- a/blueprints/schema.json
+++ b/blueprints/schema.json
@@ -7478,6 +7478,11 @@
                     "type": "string",
                     "format": "uuid",
                     "title": "Sync parent group"
+                },
+                "lookup_groups_from_user": {
+                    "type": "boolean",
+                    "title": "Lookup groups from user",
+                    "description": "Lookup group membership based on a user attribute instead of a group attribute.This allows nested group resolution on systems like FreeIPA and Active Directory"
                 }
             },
             "required": []
diff --git a/schema.yml b/schema.yml
index fbf74d3c91a9..9c698881fd1c 100644
--- a/schema.yml
+++ b/schema.yml
@@ -26595,6 +26595,10 @@ paths:
             format: uuid
         explode: true
         style: form
+      - in: query
+        name: lookup_groups_from_user
+        schema:
+          type: boolean
       - in: query
         name: name
         schema:
@@ -44480,6 +44484,11 @@ components:
           nullable: true
           description: Get cached source connectivity
           readOnly: true
+        lookup_groups_from_user:
+          type: boolean
+          description: Lookup group membership based on a user attribute instead of
+            a group attribute.This allows nested group resolution on systems like
+            FreeIPA and Active Directory
       required:
       - base_dn
       - component
@@ -44676,6 +44685,11 @@ components:
           type: string
           format: uuid
           nullable: true
+        lookup_groups_from_user:
+          type: boolean
+          description: Lookup group membership based on a user attribute instead of
+            a group attribute.This allows nested group resolution on systems like
+            FreeIPA and Active Directory
       required:
       - base_dn
       - name
@@ -49602,6 +49616,11 @@ components:
           type: string
           format: uuid
           nullable: true
+        lookup_groups_from_user:
+          type: boolean
+          description: Lookup group membership based on a user attribute instead of
+            a group attribute.This allows nested group resolution on systems like
+            FreeIPA and Active Directory
     PatchedLicenseRequest:
       type: object
       description: License Serializer
diff --git a/web/src/admin/sources/ldap/LDAPSourceForm.ts b/web/src/admin/sources/ldap/LDAPSourceForm.ts
index 7e4d3e23a7e2..b31eba3bf611 100644
--- a/web/src/admin/sources/ldap/LDAPSourceForm.ts
+++ b/web/src/admin/sources/ldap/LDAPSourceForm.ts
@@ -416,6 +416,28 @@ export class LDAPSourceForm extends BaseSourceForm<LDAPSource> {
                             )}
                         </p>
                     </ak-form-element-horizontal>
+                    <ak-form-element-horizontal name="lookupGroupsFromUser">
+                        <label class="pf-c-switch">
+                            <input
+                                class="pf-c-switch__input"
+                                type="checkbox"
+                                ?checked=${first(this.instance?.lookupGroupsFromUser, false)}
+                            />
+                            <span class="pf-c-switch__toggle">
+                                <span class="pf-c-switch__toggle-icon">
+                                    <i class="fas fa-check" aria-hidden="true"></i>
+                                </span>
+                            </span>
+                            <span class="pf-c-switch__label"
+                                >${msg("Lookup using user attribute")}</span
+                            >
+                        </label>
+                        <p class="pf-c-form__helper-text">
+                            ${msg(
+                                "Field which contains DNs of groups the user is a member of. This field is used to lookup groups from users, e.g. 'memberOf'. To lookup nested groups in an Active Directory environment use 'memberOf:1.2.840.113556.1.4.1941:'.",
+                            )}
+                        </p>
+                    </ak-form-element-horizontal>
                     <ak-form-element-horizontal
                         label=${msg("Object uniqueness field")}
                         ?required=${true}
diff --git a/website/docs/users-sources/sources/directory-sync/active-directory/index.md b/website/docs/users-sources/sources/directory-sync/active-directory/index.md
index 3b688df624f3..9d483b1356d6 100644
--- a/website/docs/users-sources/sources/directory-sync/active-directory/index.md
+++ b/website/docs/users-sources/sources/directory-sync/active-directory/index.md
@@ -62,6 +62,7 @@ Additional settings that might need to be adjusted based on the setup of your do
 - User object filter: Which objects should be considered users. For Active Directory set it to `(&(objectClass=user)(!(objectClass=computer)))` to exclude Computer accounts.
 - Group object filter: Which objects should be considered groups.
 - Group membership field: Which user field saves the group membership
+- Look up using a user attribute: Look up group memberships based on a user object attribute instead of a group attribute (`memberOf` instead of `member`). It can be useful for looking up nested group memberships, for which you'd want to use `memberOf:1.2.840.113556.1.4.1941:` as the group membership field, to tell Active Directory to follow DNs.
 - Object uniqueness field: A user field which contains a unique Identifier
 
 After you save the source, a synchronization will start in the background. When its done, you can see the summary under Dashboards -> System Tasks.