diff --git a/src/compile/standalone.rs b/src/compile/standalone.rs
index 1f603e3..2d710b1 100644
--- a/src/compile/standalone.rs
+++ b/src/compile/standalone.rs
@@ -342,17 +342,24 @@ fn generate_allowed_domains(front_matter: &FrontMatter) -> Result<String> {
 
     // Add user-specified hosts (validated against DNS-safe characters)
     for host in &user_hosts {
-        let valid = !host.is_empty()
+        let valid_chars = !host.is_empty()
             && host
                 .chars()
                 .all(|c| c.is_ascii_alphanumeric() || matches!(c, '.' | '-' | '*'));
-        if !valid {
+        if !valid_chars {
             anyhow::bail!(
                 "network.allow domain '{}' contains characters invalid in DNS names. \
                  Only ASCII alphanumerics, '.', '-', and '*' are allowed.",
                 host
             );
         }
+        if host.contains('*') && !(host.starts_with("*.") && !host[2..].contains('*')) {
+            anyhow::bail!(
+                "network.allow domain '{}' uses '*' in an unsupported position. \
+                 Wildcards must appear only as a leading prefix (e.g. '*.example.com').",
+                host
+            );
+        }
         hosts.insert(host.clone());
     }
 
diff --git a/tests/compiler_tests.rs b/tests/compiler_tests.rs
index 5204340..b19df6a 100644
--- a/tests/compiler_tests.rs
+++ b/tests/compiler_tests.rs
@@ -2522,3 +2522,219 @@ tools:
 
     let _ = fs::remove_dir_all(&temp_dir);
 }
+
+/// Test that network.allow with a valid leading wildcard (*.example.com) compiles successfully
+#[test]
+fn test_network_allow_valid_wildcard_compiles() {
+    let temp_dir = std::env::temp_dir().join(format!(
+        "agentic-pipeline-network-valid-wildcard-{}",
+        std::process::id()
+    ));
+    fs::create_dir_all(&temp_dir).expect("Failed to create temp directory");
+
+    let input = r#"---
+name: "Network Wildcard Agent"
+description: "Agent with valid leading wildcard in network.allow"
+network:
+  allow:
+    - "*.mycompany.com"
+    - "api.external-service.com"
+---
+
+## Test
+"#;
+
+    let input_path = temp_dir.join("network-valid-wildcard.md");
+    let output_path = temp_dir.join("network-valid-wildcard.yml");
+    fs::write(&input_path, input).unwrap();
+
+    let binary_path = PathBuf::from(env!("CARGO_BIN_EXE_ado-aw"));
+    let output = std::process::Command::new(&binary_path)
+        .args(["compile", input_path.to_str().unwrap(), "-o", output_path.to_str().unwrap()])
+        .output()
+        .expect("Failed to run compiler");
+
+    assert!(
+        output.status.success(),
+        "Compiler should succeed for valid wildcard '*.mycompany.com': {}",
+        String::from_utf8_lossy(&output.stderr)
+    );
+
+    let _ = fs::remove_dir_all(&temp_dir);
+}
+
+/// Test that network.allow with a trailing wildcard (example.*) fails compilation
+#[test]
+fn test_network_allow_trailing_wildcard_fails() {
+    let temp_dir = std::env::temp_dir().join(format!(
+        "agentic-pipeline-network-trailing-wildcard-{}",
+        std::process::id()
+    ));
+    fs::create_dir_all(&temp_dir).expect("Failed to create temp directory");
+
+    let input = r#"---
+name: "Network Trailing Wildcard Agent"
+description: "Agent with trailing wildcard in network.allow"
+network:
+  allow:
+    - "example.*"
+---
+
+## Test
+"#;
+
+    let input_path = temp_dir.join("network-trailing-wildcard.md");
+    let output_path = temp_dir.join("network-trailing-wildcard.yml");
+    fs::write(&input_path, input).unwrap();
+
+    let binary_path = PathBuf::from(env!("CARGO_BIN_EXE_ado-aw"));
+    let output = std::process::Command::new(&binary_path)
+        .args(["compile", input_path.to_str().unwrap(), "-o", output_path.to_str().unwrap()])
+        .output()
+        .expect("Failed to run compiler");
+
+    assert!(
+        !output.status.success(),
+        "Compiler should fail for trailing wildcard 'example.*'"
+    );
+
+    let stderr = String::from_utf8_lossy(&output.stderr);
+    assert!(
+        stderr.contains("unsupported position"),
+        "Error message should mention unsupported position: {stderr}"
+    );
+
+    let _ = fs::remove_dir_all(&temp_dir);
+}
+
+/// Test that network.allow with a mid-string wildcard (ex*ample.com) fails compilation
+#[test]
+fn test_network_allow_mid_wildcard_fails() {
+    let temp_dir = std::env::temp_dir().join(format!(
+        "agentic-pipeline-network-mid-wildcard-{}",
+        std::process::id()
+    ));
+    fs::create_dir_all(&temp_dir).expect("Failed to create temp directory");
+
+    let input = r#"---
+name: "Network Mid Wildcard Agent"
+description: "Agent with mid-string wildcard in network.allow"
+network:
+  allow:
+    - "ex*ample.com"
+---
+
+## Test
+"#;
+
+    let input_path = temp_dir.join("network-mid-wildcard.md");
+    let output_path = temp_dir.join("network-mid-wildcard.yml");
+    fs::write(&input_path, input).unwrap();
+
+    let binary_path = PathBuf::from(env!("CARGO_BIN_EXE_ado-aw"));
+    let output = std::process::Command::new(&binary_path)
+        .args(["compile", input_path.to_str().unwrap(), "-o", output_path.to_str().unwrap()])
+        .output()
+        .expect("Failed to run compiler");
+
+    assert!(
+        !output.status.success(),
+        "Compiler should fail for mid-string wildcard 'ex*ample.com'"
+    );
+
+    let stderr = String::from_utf8_lossy(&output.stderr);
+    assert!(
+        stderr.contains("unsupported position"),
+        "Error message should mention unsupported position: {stderr}"
+    );
+
+    let _ = fs::remove_dir_all(&temp_dir);
+}
+
+/// Test that network.allow with a double wildcard (*.*.com) fails compilation
+#[test]
+fn test_network_allow_double_wildcard_fails() {
+    let temp_dir = std::env::temp_dir().join(format!(
+        "agentic-pipeline-network-double-wildcard-{}",
+        std::process::id()
+    ));
+    fs::create_dir_all(&temp_dir).expect("Failed to create temp directory");
+
+    let input = r#"---
+name: "Network Double Wildcard Agent"
+description: "Agent with double wildcard in network.allow"
+network:
+  allow:
+    - "*.*.com"
+---
+
+## Test
+"#;
+
+    let input_path = temp_dir.join("network-double-wildcard.md");
+    let output_path = temp_dir.join("network-double-wildcard.yml");
+    fs::write(&input_path, input).unwrap();
+
+    let binary_path = PathBuf::from(env!("CARGO_BIN_EXE_ado-aw"));
+    let output = std::process::Command::new(&binary_path)
+        .args(["compile", input_path.to_str().unwrap(), "-o", output_path.to_str().unwrap()])
+        .output()
+        .expect("Failed to run compiler");
+
+    assert!(
+        !output.status.success(),
+        "Compiler should fail for double wildcard '*.*.com'"
+    );
+
+    let stderr = String::from_utf8_lossy(&output.stderr);
+    assert!(
+        stderr.contains("unsupported position"),
+        "Error message should mention unsupported position: {stderr}"
+    );
+
+    let _ = fs::remove_dir_all(&temp_dir);
+}
+
+/// Test that network.allow with a bare '*' fails compilation
+#[test]
+fn test_network_allow_bare_wildcard_fails() {
+    let temp_dir = std::env::temp_dir().join(format!(
+        "agentic-pipeline-network-bare-wildcard-{}",
+        std::process::id()
+    ));
+    fs::create_dir_all(&temp_dir).expect("Failed to create temp directory");
+
+    let input = r#"---
+name: "Network Bare Wildcard Agent"
+description: "Agent with bare wildcard in network.allow"
+network:
+  allow:
+    - "*"
+---
+
+## Test
+"#;
+
+    let input_path = temp_dir.join("network-bare-wildcard.md");
+    let output_path = temp_dir.join("network-bare-wildcard.yml");
+    fs::write(&input_path, input).unwrap();
+
+    let binary_path = PathBuf::from(env!("CARGO_BIN_EXE_ado-aw"));
+    let output = std::process::Command::new(&binary_path)
+        .args(["compile", input_path.to_str().unwrap(), "-o", output_path.to_str().unwrap()])
+        .output()
+        .expect("Failed to run compiler");
+
+    assert!(
+        !output.status.success(),
+        "Compiler should fail for bare wildcard '*'"
+    );
+
+    let stderr = String::from_utf8_lossy(&output.stderr);
+    assert!(
+        stderr.contains("unsupported position"),
+        "Error message should mention unsupported position: {stderr}"
+    );
+
+    let _ = fs::remove_dir_all(&temp_dir);
+}