diff --git a/authzed/api/materialize/v0/watchpermissions.proto b/authzed/api/materialize/v0/watchpermissions.proto
index dff0499..9cbc4ad 100644
--- a/authzed/api/materialize/v0/watchpermissions.proto
+++ b/authzed/api/materialize/v0/watchpermissions.proto
@@ -66,9 +66,23 @@ message WatchPermissionsResponse {
 
 message PermissionChange {
   enum Permissionship {
+    // PERMISSIONSHIP_UNSPECIFIED is the default value and should not be used.
     PERMISSIONSHIP_UNSPECIFIED = 0;
+
+    // PERMISSIONSHIP_NO_PERMISSION indicates that the subject does not have
+    // the requested permission or relationship with the resource.
     PERMISSIONSHIP_NO_PERMISSION = 1;
+
+    // PERMISSIONSHIP_HAS_PERMISSION indicates that the subject has the
+    // requested permission or relationship with the resource.
     PERMISSIONSHIP_HAS_PERMISSION = 2;
+
+    // PERMISSIONSHIP_CONDITIONAL_PERMISSION indicates that the subject may
+    // have the requested permission or relationship with the resource, but
+    // additional context is required to make a determination. This occurs
+    // when the permission depends on caveated relationships. The watcher does
+    // not provide caveat context details; consumers should query the resource
+    // directly via CheckPermission to obtain the partial_caveat_info.
     PERMISSIONSHIP_CONDITIONAL_PERMISSION = 3;
   }
 
diff --git a/authzed/api/v1/debug.proto b/authzed/api/v1/debug.proto
index 03ae189..2bf21a2 100644
--- a/authzed/api/v1/debug.proto
+++ b/authzed/api/v1/debug.proto
@@ -36,9 +36,23 @@ message CheckDebugTrace {
   }
 
   enum Permissionship {
+    // PERMISSIONSHIP_UNSPECIFIED is the default value and should not be used.
     PERMISSIONSHIP_UNSPECIFIED = 0;
+
+    // PERMISSIONSHIP_NO_PERMISSION indicates that the subject does not have
+    // the requested permission or relationship with the resource.
     PERMISSIONSHIP_NO_PERMISSION = 1;
+
+    // PERMISSIONSHIP_HAS_PERMISSION indicates that the subject has the
+    // requested permission or relationship with the resource.
     PERMISSIONSHIP_HAS_PERMISSION = 2;
+
+    // PERMISSIONSHIP_CONDITIONAL_PERMISSION indicates that the subject may
+    // have the requested permission or relationship with the resource, but
+    // additional context is required to make a determination. This occurs
+    // when the permission depends on caveated relationships and not all
+    // required context was provided in the request. See the caveat_evaluation_info
+    // field in CheckDebugTrace for the missing context.
     PERMISSIONSHIP_CONDITIONAL_PERMISSION = 3;
   }
 
diff --git a/authzed/api/v1/permission_service.proto b/authzed/api/v1/permission_service.proto
index 6337588..f920059 100644
--- a/authzed/api/v1/permission_service.proto
+++ b/authzed/api/v1/permission_service.proto
@@ -511,9 +511,23 @@ message CheckPermissionRequest {
 
 message CheckPermissionResponse {
   enum Permissionship {
+    // PERMISSIONSHIP_UNSPECIFIED is the default value and should not be used.
     PERMISSIONSHIP_UNSPECIFIED = 0;
+
+    // PERMISSIONSHIP_NO_PERMISSION indicates that the subject does not have
+    // the requested permission or relationship with the resource.
     PERMISSIONSHIP_NO_PERMISSION = 1;
+
+    // PERMISSIONSHIP_HAS_PERMISSION indicates that the subject has the
+    // requested permission or relationship with the resource.
     PERMISSIONSHIP_HAS_PERMISSION = 2;
+
+    // PERMISSIONSHIP_CONDITIONAL_PERMISSION indicates that the subject may
+    // have the requested permission or relationship with the resource, but
+    // additional context is required to make a determination. This occurs
+    // when the permission depends on caveated relationships and not all
+    // required context was provided in the request. See the partial_caveat_info
+    // field in CheckPermissionResponse for the missing context.
     PERMISSIONSHIP_CONDITIONAL_PERMISSION = 3;
   }
 
@@ -742,8 +756,19 @@ message LookupResourcesRequest {
 
 // LookupPermissionship represents whether a Lookup response was partially evaluated or not
 enum LookupPermissionship {
+  // LOOKUP_PERMISSIONSHIP_UNSPECIFIED is the default value and should not be used.
   LOOKUP_PERMISSIONSHIP_UNSPECIFIED = 0;
+
+  // LOOKUP_PERMISSIONSHIP_HAS_PERMISSION indicates that the subject has the
+  // requested permission for the resource.
   LOOKUP_PERMISSIONSHIP_HAS_PERMISSION = 1;
+
+  // LOOKUP_PERMISSIONSHIP_CONDITIONAL_PERMISSION indicates that the subject may
+  // have the requested permission for the resource, but additional context is
+  // required to make a determination. This occurs when the permission depends on
+  // caveated relationships and not all required context was provided in the request.
+  // See the partial_caveat_info field in LookupResourcesResponse and ResolvedSubject
+  // for the missing context.
   LOOKUP_PERMISSIONSHIP_CONDITIONAL_PERMISSION = 2;
 }
 
diff --git a/docs/apidocs.swagger.json b/docs/apidocs.swagger.json
index 1caa4ae..ac0f3ca 100644
--- a/docs/apidocs.swagger.json
+++ b/docs/apidocs.swagger.json
@@ -1340,7 +1340,8 @@
         "PERMISSIONSHIP_HAS_PERMISSION",
         "PERMISSIONSHIP_CONDITIONAL_PERMISSION"
       ],
-      "default": "PERMISSIONSHIP_UNSPECIFIED"
+      "default": "PERMISSIONSHIP_UNSPECIFIED",
+      "description": " - PERMISSIONSHIP_UNSPECIFIED: PERMISSIONSHIP_UNSPECIFIED is the default value and should not be used.\n - PERMISSIONSHIP_NO_PERMISSION: PERMISSIONSHIP_NO_PERMISSION indicates that the subject does not have\nthe requested permission or relationship with the resource.\n - PERMISSIONSHIP_HAS_PERMISSION: PERMISSIONSHIP_HAS_PERMISSION indicates that the subject has the\nrequested permission or relationship with the resource.\n - PERMISSIONSHIP_CONDITIONAL_PERMISSION: PERMISSIONSHIP_CONDITIONAL_PERMISSION indicates that the subject may\nhave the requested permission or relationship with the resource, but\nadditional context is required to make a determination. This occurs\nwhen the permission depends on caveated relationships and not all\nrequired context was provided in the request. See the caveat_evaluation_info\nfield in CheckDebugTrace for the missing context."
     },
     "CheckPermissionRequest": {
       "type": "object",
@@ -1404,7 +1405,8 @@
         "PERMISSIONSHIP_HAS_PERMISSION",
         "PERMISSIONSHIP_CONDITIONAL_PERMISSION"
       ],
-      "default": "PERMISSIONSHIP_UNSPECIFIED"
+      "default": "PERMISSIONSHIP_UNSPECIFIED",
+      "description": " - PERMISSIONSHIP_UNSPECIFIED: PERMISSIONSHIP_UNSPECIFIED is the default value and should not be used.\n - PERMISSIONSHIP_NO_PERMISSION: PERMISSIONSHIP_NO_PERMISSION indicates that the subject does not have\nthe requested permission or relationship with the resource.\n - PERMISSIONSHIP_HAS_PERMISSION: PERMISSIONSHIP_HAS_PERMISSION indicates that the subject has the\nrequested permission or relationship with the resource.\n - PERMISSIONSHIP_CONDITIONAL_PERMISSION: PERMISSIONSHIP_CONDITIONAL_PERMISSION indicates that the subject may\nhave the requested permission or relationship with the resource, but\nadditional context is required to make a determination. This occurs\nwhen the permission depends on caveated relationships and not all\nrequired context was provided in the request. See the partial_caveat_info\nfield in CheckPermissionResponse for the missing context."
     },
     "ComputablePermissionsRequest": {
       "type": "object",
@@ -2213,6 +2215,7 @@
         "LOOKUP_PERMISSIONSHIP_CONDITIONAL_PERMISSION"
       ],
       "default": "LOOKUP_PERMISSIONSHIP_UNSPECIFIED",
+      "description": "- LOOKUP_PERMISSIONSHIP_UNSPECIFIED: LOOKUP_PERMISSIONSHIP_UNSPECIFIED is the default value and should not be used.\n - LOOKUP_PERMISSIONSHIP_HAS_PERMISSION: LOOKUP_PERMISSIONSHIP_HAS_PERMISSION indicates that the subject has the\nrequested permission for the resource.\n - LOOKUP_PERMISSIONSHIP_CONDITIONAL_PERMISSION: LOOKUP_PERMISSIONSHIP_CONDITIONAL_PERMISSION indicates that the subject may\nhave the requested permission for the resource, but additional context is\nrequired to make a determination. This occurs when the permission depends on\ncaveated relationships and not all required context was provided in the request.\nSee the partial_caveat_info field in LookupResourcesResponse and ResolvedSubject\nfor the missing context.",
       "title": "LookupPermissionship represents whether a Lookup response was partially evaluated or not"
     },
     "LookupResourcesRequest": {
@@ -2444,7 +2447,8 @@
         "PERMISSIONSHIP_HAS_PERMISSION",
         "PERMISSIONSHIP_CONDITIONAL_PERMISSION"
       ],
-      "default": "PERMISSIONSHIP_UNSPECIFIED"
+      "default": "PERMISSIONSHIP_UNSPECIFIED",
+      "description": " - PERMISSIONSHIP_UNSPECIFIED: PERMISSIONSHIP_UNSPECIFIED is the default value and should not be used.\n - PERMISSIONSHIP_NO_PERMISSION: PERMISSIONSHIP_NO_PERMISSION indicates that the subject does not have\nthe requested permission or relationship with the resource.\n - PERMISSIONSHIP_HAS_PERMISSION: PERMISSIONSHIP_HAS_PERMISSION indicates that the subject has the\nrequested permission or relationship with the resource.\n - PERMISSIONSHIP_CONDITIONAL_PERMISSION: PERMISSIONSHIP_CONDITIONAL_PERMISSION indicates that the subject may\nhave the requested permission or relationship with the resource, but\nadditional context is required to make a determination. This occurs\nwhen the permission depends on caveated relationships. The watcher does\nnot provide caveat context details; consumers should query the resource\ndirectly via CheckPermission to obtain the partial_caveat_info."
     },
     "PermissionRelationshipTree": {
       "type": "object",