diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index a9eb266..11ebe80 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -91,8 +91,8 @@ binary needed), making it platform-independent. The downside is that custom pars
 used. This has known warts. Those warts have workarounds:
 
 - the README contains the full output of `srgn --help`, which is also tested against.
-  **This is whitespace-sensitive**, so there is trailing whitespace. Removing it fails
-  tests.
+  Run [`./scripts/update-readme.py`](./scripts/update-readme.py) to update this README
+  section automatically if you updated it.
 - the tests contain [**hard-coded names of CLI
   options**](https://github.com/alexpovel/srgn/blob/8ff54ee53ac0a53cdc4791b069648ee4511c7b94/tests/readme.rs#L494-L521).
   This is necessary as otherwise it'd be unclear if a string `--foo` should be a flag
diff --git a/scripts/update-readme.py b/scripts/update-readme.py
new file mode 100755
index 0000000..b82acba
--- /dev/null
+++ b/scripts/update-readme.py
@@ -0,0 +1,67 @@
+#!/usr/bin/env python3
+
+import argparse
+import re
+import subprocess
+from difflib import unified_diff
+from pathlib import Path
+
+ENCODING = "utf8"
+
+
+def diff(a: str, b: str, filename: Path) -> str:
+    res = "\n".join(
+        unified_diff(
+            a.splitlines(),
+            b.splitlines(),
+            fromfile=str(filename),
+            tofile=str(filename),
+        )
+    )
+    return res
+
+
+def update_markdown_file(file: Path) -> None:
+    content = file.read_text(encoding=ENCODING)
+    print(f"Got contents of {file}, {len(content)} long")
+    pattern = re.compile(
+        pattern=r"(?<=```console\n\$ srgn --help\n)(.*?)(?=```$)",
+        flags=re.DOTALL | re.MULTILINE,
+    )
+    args = ["cargo", "run", "--", "--help"]
+    result = subprocess.run(
+        args=args,
+        capture_output=True,
+        text=True,
+        check=True,
+    )
+    print(f"Successfully ran command: {args}")
+
+    match_ = re.search(pattern, content)
+    assert match_ is not None, "Bad regex/README"
+    print(f"Match at: {match_}")
+
+    new_content = re.sub(pattern, result.stdout, content)
+
+    print("Got new file contents. Diff:")
+    print(diff(content, new_content, filename=file))
+    input("Press Enter to confirm and write to file, CTRL+C to abort...")
+    file.write_text(new_content, encoding=ENCODING)
+    print("Wrote new file contents.")
+
+
+def main():
+    parser = argparse.ArgumentParser(
+        description="Update Markdown console code blocks with actual command output"
+    )
+    parser.add_argument("file", help="Path to the Markdown file to process")
+    args = parser.parse_args()
+
+    file = Path(args.file)
+    update_markdown_file(file)
+    print(f"Successfully updated {file}")
+    print("Done")
+
+
+if __name__ == "__main__":
+    main()
diff --git a/tests/readme.rs b/tests/readme.rs
index 70dde68..6615a26 100644
--- a/tests/readme.rs
+++ b/tests/readme.rs
@@ -818,6 +818,8 @@ mod tests {
 
     #[test]
     fn test_readme_code_blocks() {
+        let _helper = TestHinter;
+
         let snippets = get_readme_snippets();
         let pipes = get_readme_program_pipes(&snippets);
 
@@ -949,4 +951,18 @@ mod tests {
 
         res
     }
+
+    struct TestHinter;
+
+    impl Drop for TestHinter {
+        fn drop(&mut self) {
+            if std::thread::panicking() {
+                println!("\n==============================================");
+                println!("💡 README test failed!");
+                println!("Did you update the `srgn --help` output?");
+                println!("If no, run `./scripts/update-readme.py README.md` and try again.");
+                println!("==============================================\n");
+            }
+        }
+    }
 }