diff --git a/SpiceDb/Api/SpiceDbPermissions.cs b/SpiceDb/Api/SpiceDbPermissions.cs
index eedd2a2..c055a9b 100644
--- a/SpiceDb/Api/SpiceDbPermissions.cs
+++ b/SpiceDb/Api/SpiceDbPermissions.cs
@@ -1,6 +1,7 @@
 using Authzed.Api.V1;
 using Google.Protobuf;
 using Google.Protobuf.Collections;
+using Google.Protobuf.WellKnownTypes;
 using Grpc.Core;
 using SpiceDb.Enum;
 using SpiceDb.Models;
@@ -396,7 +397,7 @@ public bool UpdateRelationships(ref RepeatedField<RelationshipUpdate> updateColl
 
     public RelationshipUpdate GetRelationshipUpdate(string resourceType, string resourceId,
            string relation, string subjectType, string subjectId, string optionalSubjectRelation = "",
-           RelationshipUpdate.Types.Operation operation = RelationshipUpdate.Types.Operation.Touch)
+           RelationshipUpdate.Types.Operation operation = RelationshipUpdate.Types.Operation.Touch, Caveat? caveat = null)
     {
         return new RelationshipUpdate
         {
@@ -406,6 +407,7 @@ public RelationshipUpdate GetRelationshipUpdate(string resourceType, string reso
                 Resource = new ObjectReference { ObjectType = resourceType, ObjectId = resourceId },
                 Relation = relation,
                 Subject = new SubjectReference { Object = new ObjectReference { ObjectType = subjectType, ObjectId = subjectId }, OptionalRelation = optionalSubjectRelation },
+                OptionalCaveat = GetCaveat(caveat)
             }
         };
     }
@@ -426,21 +428,21 @@ public async Task<WriteRelationshipsResponse> WriteRelationshipsAsync(RepeatedFi
 
     public async Task<ZedToken> UpdateRelationshipAsync(string resourceType, string resourceId, string relation,
            string subjectType, string subjectId, string optionalSubjectRelation = "",
-          RelationshipUpdate.Types.Operation operation = RelationshipUpdate.Types.Operation.Touch)
+          RelationshipUpdate.Types.Operation operation = RelationshipUpdate.Types.Operation.Touch, Caveat? caveat = null)
     {
 
-        return await UpdateRelationshipsAsync(resourceType, resourceId, new[] { relation }, subjectType, subjectId, optionalSubjectRelation, operation);
+        return await UpdateRelationshipsAsync(resourceType, resourceId, new[] { relation }, subjectType, subjectId, optionalSubjectRelation, operation, caveat);
     }
 
     public async Task<ZedToken> UpdateRelationshipsAsync(string resourceType, string resourceId, IEnumerable<string> relations,
             string subjectType, string subjectId, string optionalSubjectRelation = "",
-           RelationshipUpdate.Types.Operation operation = RelationshipUpdate.Types.Operation.Touch)
+           RelationshipUpdate.Types.Operation operation = RelationshipUpdate.Types.Operation.Touch, Caveat? caveat = null)
     {
         RepeatedField<RelationshipUpdate> updateCollection = new RepeatedField<RelationshipUpdate>();
 
         foreach (var relation in relations)
         {
-            var updateItem = GetRelationshipUpdate(resourceType, resourceId, relation.ToLowerInvariant(), subjectType, subjectId, optionalSubjectRelation, operation);
+            var updateItem = GetRelationshipUpdate(resourceType, resourceId, relation.ToLowerInvariant(), subjectType, subjectId, optionalSubjectRelation, operation, caveat);
             UpdateRelationships(ref updateCollection, updateItem);
         }
 
@@ -448,4 +450,17 @@ public async Task<ZedToken> UpdateRelationshipsAsync(string resourceType, string
         return resp.WrittenAt;
     }
 
+    protected ContextualizedCaveat? GetCaveat(Caveat? caveat)
+    {
+        if (caveat is null)
+        {
+            return null;
+        }
+
+        return new ContextualizedCaveat
+        {
+            CaveatName = caveat.Name,
+            Context = caveat.Context?.ToStruct(),
+        };
+    }
 }
\ No newline at end of file
diff --git a/SpiceDb/Models/Relationship.cs b/SpiceDb/Models/Relationship.cs
index c76c8f9..f7da306 100644
--- a/SpiceDb/Models/Relationship.cs
+++ b/SpiceDb/Models/Relationship.cs
@@ -7,6 +7,7 @@ public Relationship(ResourceReference resource, string relation, ResourceReferen
         Resource = resource;
         Relation = relation;
         Subject = subject;
+        OptionalCaveat = optionalCaveat;
 
         if (!string.IsNullOrEmpty(Resource.Relation))
         {
diff --git a/SpiceDb/SpiceDbClient.cs b/SpiceDb/SpiceDbClient.cs
index ec787e6..5b1b65b 100644
--- a/SpiceDb/SpiceDbClient.cs
+++ b/SpiceDb/SpiceDbClient.cs
@@ -161,7 +161,7 @@ public async IAsyncEnumerable<ReadRelationshipsResponse> ReadRelationshipsAsync(
 				OptionalCaveat = x.Relationship.OptionalCaveat != null
 					? new Authzed.Api.V1.ContextualizedCaveat
 					{
-						CaveatName = x.Relationship.OptionalCaveat.Name,
+						CaveatName = EnsurePrefix(x.Relationship.OptionalCaveat.Name)!,
 						Context = x.Relationship.OptionalCaveat.Context.ToStruct()
 					}
 					: null
@@ -370,7 +370,7 @@ private PermissionRelationshipTree BuildTree(Authzed.Api.V1.PermissionRelationsh
 		var request = relationships.Select(x => new RelationshipUpdate
 		{
 			Relationship = new Relationship(
-				x.Resource.EnsurePrefix(_prefix), x.Relation, x.Subject.EnsurePrefix(_prefix), x.OptionalCaveat
+				x.Resource.EnsurePrefix(_prefix), x.Relation, x.Subject.EnsurePrefix(_prefix), EnsureCaveatIsPrefixed(x.OptionalCaveat)
 			),
 			Operation = RelationshipUpdateOperation.Upsert
 		}).ToList();
@@ -387,7 +387,7 @@ public async Task<ZedToken> AddRelationshipAsync(Relationship relation)
 	{
 		return (await _spiceDbCore.Permissions.UpdateRelationshipAsync(EnsurePrefix(relation.Resource.Type)!,
 				relation.Resource.Id, relation.Relation, EnsurePrefix(relation.Subject.Type)!, relation.Subject.Id,
-				relation.Subject.Relation))
+				relation.Subject.Relation, caveat: EnsureCaveatIsPrefixed(relation.OptionalCaveat)))
 			.ToSpiceDbToken()!;
 	}
 
@@ -627,4 +627,15 @@ public async Task ImportSchemaFromStringAsync(string schema)
 
 		return type.StartsWith(_prefix + "/") ? type : $"{_prefix}/{type}";
 	}
+
+	private Caveat? EnsureCaveatIsPrefixed(Caveat? caveat)
+	{
+		if (caveat is null)
+		{
+			return null;
+		}
+
+		caveat.Name = EnsurePrefix(caveat.Name)!;
+		return caveat;
+	}
 }
\ No newline at end of file