diff --git a/README.md b/README.md
index 10d2d6e..c8f1c69 100644
--- a/README.md
+++ b/README.md
@@ -55,6 +55,11 @@ The following environment variables configure AI-powered photo insights and dail
   - Used to fetch conversation data for context in insights
 - `SMS_API_TOKEN` - Authentication token for SMS API (optional)
 
+#### Agentic Insight Generation
+- `AGENTIC_MAX_ITERATIONS` - Maximum tool-call iterations per agentic insight request [default: `10`]
+  - Controls how many times the model can invoke tools before being forced to produce a final answer
+  - Increase for more thorough context gathering; decrease to limit response time
+
 #### Fallback Behavior
 - Primary server is tried first with 5-second connection timeout
 - On failure, automatically falls back to secondary server (if configured)
diff --git a/src/ai/insight_generator.rs b/src/ai/insight_generator.rs
index 6434314..2027fd2 100644
--- a/src/ai/insight_generator.rs
+++ b/src/ai/insight_generator.rs
@@ -1803,7 +1803,32 @@ Return ONLY the summary, nothing else."#,
 
         let insight_cx = current_cx.with_span(span);
 
-        // 2. Check tool calling capability
+        // 2a. Verify the model exists on at least one server before checking capabilities
+        if let Some(ref model_name) = custom_model {
+            let available_on_primary = OllamaClient::is_model_available(
+                &ollama_client.primary_url,
+                model_name,
+            )
+            .await
+            .unwrap_or(false);
+
+            let available_on_fallback = if let Some(ref fallback_url) = ollama_client.fallback_url {
+                OllamaClient::is_model_available(fallback_url, model_name)
+                    .await
+                    .unwrap_or(false)
+            } else {
+                false
+            };
+
+            if !available_on_primary && !available_on_fallback {
+                anyhow::bail!(
+                    "model not available: '{}' not found on any configured server",
+                    model_name
+                );
+            }
+        }
+
+        // 2b. Check tool calling capability
         let capabilities = OllamaClient::check_model_capabilities(
             &ollama_client.primary_url,
             &ollama_client.primary_model,