diff --git a/gateway/src/adapters/telegram.rs b/gateway/src/adapters/telegram.rs
index ee5d08dd1..5ce433007 100644
--- a/gateway/src/adapters/telegram.rs
+++ b/gateway/src/adapters/telegram.rs
@@ -332,7 +332,7 @@ pub async fn handle_reply(
         "gateway → telegram"
     );
     let url = format!("{TELEGRAM_API_BASE}/bot{bot_token}/sendMessage");
-    let _ = client
+    let retry_plain = match client
         .post(&url)
         .json(&serde_json::json!({
             "chat_id": reply.channel.id,
@@ -342,7 +342,68 @@ pub async fn handle_reply(
         }))
         .send()
         .await
-        .map_err(|e| error!("telegram send error: {e}"));
+    {
+        Ok(resp) => {
+            match resp.json::<serde_json::Value>().await {
+                Ok(body) if body["ok"].as_bool() != Some(true) => {
+                    let desc = body["description"].as_str().unwrap_or("unknown");
+                    let code = body["error_code"].as_u64().unwrap_or(0);
+                    if should_retry_plain_text_fallback(code, desc) {
+                        warn!(code, desc = %desc, "telegram Markdown parse failed, retrying as plain text");
+                        true
+                    } else {
+                        error!(code, desc = %desc, "telegram send failed");
+                        false
+                    }
+                }
+                Ok(_) => false,
+                Err(e) => {
+                    warn!("telegram response not valid JSON: {e}");
+                    false
+                }
+            }
+        }
+        Err(e) => {
+            error!("telegram send error: {e}");
+            false
+        }
+    };
+
+    if retry_plain {
+        match client
+            .post(&url)
+            .json(&serde_json::json!({
+                "chat_id": reply.channel.id,
+                "text": reply.content.text,
+                "message_thread_id": reply.channel.thread_id,
+            }))
+            .send()
+            .await
+        {
+            Ok(resp) => {
+                match resp.json::<serde_json::Value>().await {
+                    Ok(body) if body["ok"].as_bool() != Some(true) => {
+                        error!(
+                            desc = %body["description"].as_str().unwrap_or("unknown"),
+                            "telegram plain text fallback also failed"
+                        );
+                    }
+                    Err(e) => warn!("telegram plain text fallback response not valid JSON: {e}"),
+                    _ => {}
+                }
+            }
+            Err(e) => error!("telegram plain text send error: {e}"),
+        }
+    }
+}
+
+fn should_retry_plain_text_fallback(code: u64, description: &str) -> bool {
+    if code != 400 {
+        return false;
+    }
+
+    let description = description.to_ascii_lowercase();
+    description.contains("parse") || description.contains("entities")
 }
 
 /// Download media from Telegram via getFile → store to filesystem (colocate mode).
@@ -483,3 +544,40 @@ async fn download_telegram_document(
         path: Some(path),
     })
 }
+
+#[cfg(test)]
+mod tests {
+    use super::should_retry_plain_text_fallback;
+
+    #[test]
+    fn retries_markdown_parse_errors() {
+        assert!(should_retry_plain_text_fallback(
+            400,
+            "Bad Request: can't parse entities: Can't find end of the entity"
+        ));
+    }
+
+    #[test]
+    fn retries_entity_errors() {
+        assert!(should_retry_plain_text_fallback(
+            400,
+            "Bad Request: unsupported start tag in entities"
+        ));
+    }
+
+    #[test]
+    fn does_not_retry_unrelated_bad_requests() {
+        assert!(!should_retry_plain_text_fallback(
+            400,
+            "Bad Request: message text is empty"
+        ));
+    }
+
+    #[test]
+    fn does_not_retry_non_bad_request_errors() {
+        assert!(!should_retry_plain_text_fallback(
+            429,
+            "Too Many Requests: retry after 10"
+        ));
+    }
+}