diff --git a/pkg/api/handlers/agent.go b/pkg/api/handlers/agent.go
index 4060397f..72f2af7f 100644
--- a/pkg/api/handlers/agent.go
+++ b/pkg/api/handlers/agent.go
@@ -223,7 +223,7 @@ func (a *AgentHandler) UploadKnowledge(ctx context.Context, req api.Request) err
 		return err
 	}
 
-	agent.Status.IngestKnowledge = true
+	agent.Status.KnowledgeGeneration++
 	agent.Status.HasKnowledge = true
 	return req.Storage.Status().Update(ctx, &agent)
 }
@@ -248,7 +248,7 @@ func (a *AgentHandler) DeleteKnowledge(ctx context.Context, req api.Request) err
 		return fmt.Errorf("failed to list files in workspace %s: %w", agent.Status.KnowledgeWorkspaceID, err)
 	}
 
-	agent.Status.IngestKnowledge = true
+	agent.Status.KnowledgeGeneration++
 	agent.Status.HasKnowledge = len(files) > 0
 	return req.Storage.Status().Update(ctx, &agent)
 }
@@ -273,6 +273,6 @@ func (a *AgentHandler) IngestKnowledge(ctx context.Context, req api.Request) err
 		return nil
 	}
 
-	agent.Status.IngestKnowledge = true
+	agent.Status.KnowledgeGeneration++
 	return req.Storage.Status().Update(ctx, &agent)
 }
diff --git a/pkg/api/handlers/threads.go b/pkg/api/handlers/threads.go
index c647078c..4fa2f843 100644
--- a/pkg/api/handlers/threads.go
+++ b/pkg/api/handlers/threads.go
@@ -110,7 +110,7 @@ func (a *ThreadHandler) UploadKnowledge(ctx context.Context, req api.Request) er
 		return err
 	}
 
-	thread.Status.IngestKnowledge = true
+	thread.Status.KnowledgeGeneration++
 	thread.Status.HasKnowledge = true
 	return req.Storage.Status().Update(ctx, &thread)
 }
@@ -135,7 +135,7 @@ func (a *ThreadHandler) DeleteKnowledge(ctx context.Context, req api.Request) er
 		return fmt.Errorf("failed to list files in workspace %s: %w", thread.Spec.KnowledgeWorkspaceID, err)
 	}
 
-	thread.Status.IngestKnowledge = true
+	thread.Status.KnowledgeGeneration++
 	thread.Status.HasKnowledge = len(files) > 0
 	return req.Storage.Status().Update(ctx, &thread)
 }
@@ -160,6 +160,6 @@ func (a *ThreadHandler) IngestKnowledge(ctx context.Context, req api.Request) er
 		return nil
 	}
 
-	thread.Status.IngestKnowledge = true
+	thread.Status.KnowledgeGeneration++
 	return req.Storage.Status().Update(ctx, &thread)
 }
diff --git a/pkg/controller/handlers/agents/agents.go b/pkg/controller/handlers/agents/agents.go
index 02728be4..47ac845d 100644
--- a/pkg/controller/handlers/agents/agents.go
+++ b/pkg/controller/handlers/agents/agents.go
@@ -54,7 +54,7 @@ func (a *AgentHandler) RemoveWorkspaces(req router.Request, resp router.Response
 
 func (a *AgentHandler) IngestKnowledge(req router.Request, resp router.Response) error {
 	agent := req.Object.(*v1.Agent)
-	if !agent.Status.IngestKnowledge || !agent.Status.HasKnowledge {
+	if agent.Status.KnowledgeGeneration == agent.Status.ObservedKnowledgeGeneration || !agent.Status.HasKnowledge {
 		return nil
 	}
 
@@ -62,6 +62,6 @@ func (a *AgentHandler) IngestKnowledge(req router.Request, resp router.Response)
 		return err
 	}
 
-	agent.Status.IngestKnowledge = false
+	agent.Status.ObservedKnowledgeGeneration = agent.Status.KnowledgeGeneration
 	return nil
 }
diff --git a/pkg/controller/handlers/threads/threads.go b/pkg/controller/handlers/threads/threads.go
index 69c7cfae..bb0b3eac 100644
--- a/pkg/controller/handlers/threads/threads.go
+++ b/pkg/controller/handlers/threads/threads.go
@@ -58,7 +58,7 @@ func (t *ThreadHandler) RemoveWorkspaces(req router.Request, resp router.Respons
 
 func (t *ThreadHandler) IngestKnowledge(req router.Request, resp router.Response) error {
 	thread := req.Object.(*v1.Thread)
-	if !thread.Status.IngestKnowledge || !thread.Status.HasKnowledge {
+	if thread.Status.KnowledgeGeneration == thread.Status.ObservedKnowledgeGeneration || !thread.Status.HasKnowledge {
 		return nil
 	}
 
@@ -66,6 +66,6 @@ func (t *ThreadHandler) IngestKnowledge(req router.Request, resp router.Response
 		return err
 	}
 
-	thread.Status.IngestKnowledge = false
+	thread.Status.ObservedKnowledgeGeneration = thread.Status.KnowledgeGeneration
 	return nil
 }
diff --git a/pkg/storage/apis/otto.gptscript.ai/v1/agent.go b/pkg/storage/apis/otto.gptscript.ai/v1/agent.go
index 867da18a..126e89f7 100644
--- a/pkg/storage/apis/otto.gptscript.ai/v1/agent.go
+++ b/pkg/storage/apis/otto.gptscript.ai/v1/agent.go
@@ -34,11 +34,12 @@ type AgentSpec struct {
 }
 
 type AgentStatus struct {
-	Conditions           []metav1.Condition `json:"conditions,omitempty"`
-	HasKnowledge         bool               `json:"hasKnowledge,omitempty"`
-	IngestKnowledge      bool               `json:"ingestKnowledge,omitempty"`
-	WorkspaceID          string             `json:"workspaceID,omitempty"`
-	KnowledgeWorkspaceID string             `json:"knowledgeWorkspaceID,omitempty"`
+	Conditions                  []metav1.Condition `json:"conditions,omitempty"`
+	HasKnowledge                bool               `json:"hasKnowledge,omitempty"`
+	KnowledgeGeneration         int64              `json:"knowledgeGeneration,omitempty"`
+	ObservedKnowledgeGeneration int64              `json:"observedKnowledgeGeneration,omitempty"`
+	WorkspaceID                 string             `json:"workspaceID,omitempty"`
+	KnowledgeWorkspaceID        string             `json:"knowledgeWorkspaceID,omitempty"`
 }
 
 // +k8s:deepcopy-gen:interfaces=k8s.io/apimachinery/pkg/runtime.Object
diff --git a/pkg/storage/apis/otto.gptscript.ai/v1/thread.go b/pkg/storage/apis/otto.gptscript.ai/v1/thread.go
index a4256cf5..8359200d 100644
--- a/pkg/storage/apis/otto.gptscript.ai/v1/thread.go
+++ b/pkg/storage/apis/otto.gptscript.ai/v1/thread.go
@@ -33,14 +33,15 @@ type ThreadSpec struct {
 }
 
 type ThreadStatus struct {
-	Description     string                   `json:"description,omitempty"`
-	LastRunName     string                   `json:"lastRunName,omitempty"`
-	LastRunState    gptscriptclient.RunState `json:"lastRunState,omitempty"`
-	LastRunOutput   string                   `json:"lastRunOutput,omitempty"`
-	LastRunError    string                   `json:"lastRunError,omitempty"`
-	Conditions      []metav1.Condition       `json:"conditions,omitempty"`
-	HasKnowledge    bool                     `json:"hasKnowledge,omitempty"`
-	IngestKnowledge bool                     `json:"ingestKnowledge,omitempty"`
+	Description                 string                   `json:"description,omitempty"`
+	LastRunName                 string                   `json:"lastRunName,omitempty"`
+	LastRunState                gptscriptclient.RunState `json:"lastRunState,omitempty"`
+	LastRunOutput               string                   `json:"lastRunOutput,omitempty"`
+	LastRunError                string                   `json:"lastRunError,omitempty"`
+	Conditions                  []metav1.Condition       `json:"conditions,omitempty"`
+	HasKnowledge                bool                     `json:"hasKnowledge,omitempty"`
+	KnowledgeGeneration         int64                    `json:"knowledgeGeneration,omitempty"`
+	ObservedKnowledgeGeneration int64                    `json:"observedKnowledgeGeneration,omitempty"`
 }
 
 // +k8s:deepcopy-gen:interfaces=k8s.io/apimachinery/pkg/runtime.Object
diff --git a/pkg/storage/openapi/generated/openapi_generated.go b/pkg/storage/openapi/generated/openapi_generated.go
index 2f132025..2dc42f0a 100644
--- a/pkg/storage/openapi/generated/openapi_generated.go
+++ b/pkg/storage/openapi/generated/openapi_generated.go
@@ -369,10 +369,16 @@ func schema_storage_apis_ottogptscriptai_v1_AgentStatus(ref common.ReferenceCall
 							Format: "",
 						},
 					},
-					"ingestKnowledge": {
+					"knowledgeGeneration": {
 						SchemaProps: spec.SchemaProps{
-							Type:   []string{"boolean"},
-							Format: "",
+							Type:   []string{"integer"},
+							Format: "int64",
+						},
+					},
+					"observedKnowledgeGeneration": {
+						SchemaProps: spec.SchemaProps{
+							Type:   []string{"integer"},
+							Format: "int64",
 						},
 					},
 					"workspaceID": {
@@ -1178,10 +1184,16 @@ func schema_storage_apis_ottogptscriptai_v1_ThreadStatus(ref common.ReferenceCal
 							Format: "",
 						},
 					},
-					"ingestKnowledge": {
+					"knowledgeGeneration": {
 						SchemaProps: spec.SchemaProps{
-							Type:   []string{"boolean"},
-							Format: "",
+							Type:   []string{"integer"},
+							Format: "int64",
+						},
+					},
+					"observedKnowledgeGeneration": {
+						SchemaProps: spec.SchemaProps{
+							Type:   []string{"integer"},
+							Format: "int64",
 						},
 					},
 				},