diff --git a/contrib/tinyweb/example_auth.ae b/contrib/tinyweb/example_auth.ae
index 8d4f265c6..b8e8220b0 100644
--- a/contrib/tinyweb/example_auth.ae
+++ b/contrib/tinyweb/example_auth.ae
@@ -55,16 +55,23 @@ main() {
         }
     }
 
-    println("Starting server on localhost:8080...")
-    println("")
-    println("Test the auth flow:")
-    println("  curl http://localhost:8080/api/profile")
-    println("    -> 403 Try logging in again")
-    println("")
-    println("  curl -H 'Cookie: session=valid-session-abc' http://localhost:8080/api/profile")
-    println("    -> 200 User is logged in: alice@example.com")
+    http.monitor(tinyweb.http_server(server)) {
+        listening() |host: string, port: int| {
+            println("Test the auth flow:")
+            println("  curl http://localhost:${port}/api/profile")
+            println("    -> 403 Try logging in again")
+            println("")
+            println("  curl -H 'Cookie: session=valid-session-abc' http://localhost:${port}/api/profile")
+            println("    -> 200 User is logged in: alice@example.com")
+            println("\nPress Ctrl+C to stop.")
+        }
+    }
 
+    println("Starting server on localhost:8080...")
     result = tinyweb.tw_start(server)
-    if result != "" { println("ERROR: Failed to start server: ${result}") }
+    if result != "" {
+        println("ERROR: Failed to start server: ${result}")
+    }
+
     tinyweb.tw_stop(server)
 }
diff --git a/contrib/tinyweb/example_composition.ae b/contrib/tinyweb/example_composition.ae
index ef1b03fad..d056dfaa5 100644
--- a/contrib/tinyweb/example_composition.ae
+++ b/contrib/tinyweb/example_composition.ae
@@ -75,19 +75,23 @@ main() {
         }
     }
 
+    http.monitor(tinyweb.http_server(server)) {
+        listening() |host: string, port: int| {
+            println("Server running! Try:")
+            println("  curl http://localhost:${port}/api/v1/health")
+            println("  curl http://localhost:${port}/api/v1/greeting/Jane/Doe")
+            println("  curl -H 'X-Admin-Token: secret42' http://localhost:${port}/admin/dashboard")
+            println("  curl http://localhost:${port}/admin/dashboard    # -> 403")
+            println("  curl http://localhost:${port}/shop/catalog/products/99")
+            println("  curl http://localhost:${port}/extra/ping")
+            println("\nPress Ctrl+C to stop.")
+        }
+    }
+
     println("Starting server on localhost:8080...")
     result = tinyweb.tw_start(server)
-
-    if result == "" {
-        println("Server running! Try:")
-        println("  curl http://localhost:8080/api/v1/health")
-        println("  curl http://localhost:8080/api/v1/greeting/Jane/Doe")
-        println("  curl -H 'X-Admin-Token: secret42' http://localhost:8080/admin/dashboard")
-        println("  curl http://localhost:8080/admin/dashboard    # -> 403")
-        println("  curl http://localhost:8080/shop/catalog/products/99")
-        println("  curl http://localhost:8080/extra/ping")
-    } else {
-        println("ERROR: Failed to start server")
+    if result != "" {
+        println("ERROR: Failed to start server: ${result}")
     }
 
     tinyweb.tw_stop(server)
diff --git a/contrib/tinyweb/example_sse.ae b/contrib/tinyweb/example_sse.ae
index 291ed2fe3..711babf1b 100644
--- a/contrib/tinyweb/example_sse.ae
+++ b/contrib/tinyweb/example_sse.ae
@@ -1,6 +1,7 @@
 // Server-Sent Events (SSE) and chunked Example — streaming to browser clients
 
 import contrib.tinyweb
+import std.http
 
 main() {
     println("=== TinyWeb SSE + Chunked Example ===\n")
@@ -58,10 +59,19 @@ main() {
         }
     }
 
-    println("Open http://localhost:8080/ or: curl -N http://localhost:8080/sse/events")
-    println("Chunked: curl -N http://localhost:8080/countdown")
+    http.monitor(tinyweb.http_server(server)) {
+        listening() |host: string, port: int| {
+            println("Open http://localhost:${port}/ or: curl -N http://localhost:${port}/sse/events")
+            println("Chunked: curl -N http://localhost:${port}/countdown")
+            println("\nPress Ctrl+C to stop.")
+        }
+    }
 
+    println("Starting server on localhost:8080...")
     result = tinyweb.tw_start(server)
-    if result != "" { println("ERROR: Failed to start server: ${result}") }
+    if result != "" {
+        println("ERROR: Failed to start server: ${result}")
+    }
+
     tinyweb.tw_stop(server)
 }
diff --git a/contrib/tinyweb/example_static.ae b/contrib/tinyweb/example_static.ae
index e18d75901..9f1b2ef40 100644
--- a/contrib/tinyweb/example_static.ae
+++ b/contrib/tinyweb/example_static.ae
@@ -36,12 +36,21 @@ main() {
         }
     }
 
-    println("Starting server on localhost:8080...")
-    println("  http://localhost:8080/              — index page")
-    println("  http://localhost:8080/static/...    — static files from cwd")
-    println("  http://localhost:8080/api/health    — JSON health check")
+    http.monitor(tinyweb.http_server(server)) {
+        listening() |host: string, port: int| {
+            println("Server running! Try:")
+            println("  http://localhost:${port}/              — index page")
+            println("  http://localhost:${port}/static/...    — static files from cwd")
+            println("  http://localhost:${port}/api/health    — JSON health check")
+            println("\nPress Ctrl+C to stop.")
+        }
+    }
 
+    println("Starting server on localhost:8080...")
     result = tinyweb.tw_start(server)
-    if result != "" { println("ERROR: Failed to start server: ${result}") }
+    if result != "" {
+        println("ERROR: Failed to start server: ${result}")
+    }
+
     tinyweb.tw_stop(server)
 }
diff --git a/contrib/tinyweb/example_websocket.ae b/contrib/tinyweb/example_websocket.ae
index 36083946f..1eb89a40c 100644
--- a/contrib/tinyweb/example_websocket.ae
+++ b/contrib/tinyweb/example_websocket.ae
@@ -48,12 +48,21 @@ main() {
         }
     }
 
-    println("Open http://localhost:8080/ in a browser for the demo page.")
-    println("  ws://localhost:8080/echo     — simple echo")
-    println("  ws://localhost:8080/foo/eee  — echo x3")
+    http.monitor(tinyweb.http_server(server)) {
+        listening() |host: string, port: int| {
+            println("Open http://localhost:${port}/ in a browser for the demo page.")
+            println("  ws://localhost:${port}/echo     — simple echo")
+            println("  ws://localhost:${port}/foo/eee  — echo x3")
+            println("\nPress Ctrl+C to stop.")
+        }
+    }
 
+    println("Starting server on localhost:8080...")
     result = tinyweb.tw_start(server)
-    if result != "" { println("ERROR: Failed to start server: ${result}") }
+    if result != "" {
+        println("ERROR: Failed to start server: ${result}")
+    }
+
     tinyweb.tw_stop(server)
     println("Server stopped.")
 }
diff --git a/new_changelogs/20261029T183900Z-changed-tinyweb-example-hints.md b/new_changelogs/20261029T183900Z-changed-tinyweb-example-hints.md
new file mode 100644
index 000000000..afe680e8a
--- /dev/null
+++ b/new_changelogs/20261029T183900Z-changed-tinyweb-example-hints.md
@@ -0,0 +1,6 @@
+- **The TinyWeb examples print their usage hints once the server is
+  listening.** `example_auth`, `example_composition`, `example_sse`,
+  `example_static` and `example_websocket` printed curl hints before
+  `tw_start`, so the hints appeared even when the bind failed, and named a
+  hard-coded port. They now print from `http.monitor`'s `listening` callback
+  with the bound port, as `example_app` does.