diff --git a/.chronus/changes/fix-ci-readme-regeneration-2026-5-14.md b/.chronus/changes/fix-ci-readme-regeneration-2026-5-14.md
new file mode 100644
index 00000000000..a5fd88faafd
--- /dev/null
+++ b/.chronus/changes/fix-ci-readme-regeneration-2026-5-14.md
@@ -0,0 +1,7 @@
+---
+changeKind: internal
+packages:
+  - "@typespec/http-client-python"
+---
+
+Fix CI on main by deleting README.md files during baseline reset so regeneration recreates them; extend unit test to assert README.md exists for every generated SDK package (azure & unbranded).
diff --git a/packages/http-client-python/eng/scripts/ci/regenerate-common.ts b/packages/http-client-python/eng/scripts/ci/regenerate-common.ts
index f21c4013616..529270f1d1d 100644
--- a/packages/http-client-python/eng/scripts/ci/regenerate-common.ts
+++ b/packages/http-client-python/eng/scripts/ci/regenerate-common.ts
@@ -732,16 +732,23 @@ export async function prepareBaselineOfGeneratedCode(generatedFolder: string): P
     rmSync(tempDir, { recursive: true, force: true });
   }
 
-  // Delete a couple of fully-generated package folders so regeneration has to
-  // recreate them from scratch (smoke test of full-emit path).
-  const targetsToDelete = [
-    join(testsGeneratedDir, "azure", "authentication-http-custom"),
-    join(testsGeneratedDir, "unbranded", "encode-array"),
-  ];
-  for (const target of targetsToDelete) {
-    if (existsSync(target)) {
-      console.log(pc.dim(`Deleting ${target}`));
-      rmSync(target, { recursive: true, force: true });
+  // Smoke test the full-emit path: delete a couple of fully-generated package
+  // folders and every README.md so regeneration has to recreate them.
+  const deleteIfExists = (path: string) => {
+    if (!existsSync(path)) return;
+    console.log(pc.dim(`Deleting ${path}`));
+    rmSync(path, { recursive: true, force: true });
+  };
+
+  deleteIfExists(join(testsGeneratedDir, "azure", "authentication-http-custom"));
+  deleteIfExists(join(testsGeneratedDir, "unbranded", "encode-array"));
+
+  if (existsSync(testsGeneratedDir)) {
+    const entries = await readdir(testsGeneratedDir, { recursive: true, withFileTypes: true });
+    for (const entry of entries) {
+      if (entry.isFile() && entry.name === "README.md") {
+        deleteIfExists(join(entry.parentPath, entry.name));
+      }
     }
   }
 }
diff --git a/packages/http-client-python/package.json b/packages/http-client-python/package.json
index b4edd33cca2..a6c894ec804 100644
--- a/packages/http-client-python/package.json
+++ b/packages/http-client-python/package.json
@@ -26,7 +26,7 @@
     }
   },
   "engines": {
-    "node": ">=20.0.0"
+    "node": ">=22.0.0"
   },
   "scripts": {
     "clean": "rimraf ./dist ./temp ./venv ./tests/generated",
diff --git a/packages/http-client-python/tests/mock_api/shared/unittests/test_readme.py b/packages/http-client-python/tests/mock_api/shared/unittests/test_readme.py
new file mode 100644
index 00000000000..133f680d9e7
--- /dev/null
+++ b/packages/http-client-python/tests/mock_api/shared/unittests/test_readme.py
@@ -0,0 +1,46 @@
+from pathlib import Path
+
+import pytest
+
+GENERATED_DIR = Path(__file__).parent / "../../../generated"
+FLAVORS = ("azure", "unbranded")
+
+# Folders that exist in the azure-sdk-for-python baseline checkout but are not
+# regenerated by the emitter, so their README.md is never (re)written. Skip
+# them to keep this test focused on real generated packages.
+#   - "azure/service-multiple-services": listed in SKIP_SPECS in
+#     eng/scripts/ci/regenerate-common.ts (no emitter run for this spec).
+#   - "azure/azure-client-generator-core-client-initialization": orphan parent
+#     folder; only its sub-specs (.../default, .../individually,
+#     .../individuallyParent) are actually emitted as packages.
+SKIP_PACKAGES = {
+    ("azure", "service-multiple-services"),
+    ("azure", "azure-client-generator-core-client-initialization"),
+}
+
+
+def _package_dirs():
+    base = GENERATED_DIR.resolve()
+    dirs = []
+    for flavor in FLAVORS:
+        flavor_dir = base / flavor
+        if not flavor_dir.is_dir():
+            continue
+        for p in sorted(flavor_dir.iterdir()):
+            if not p.is_dir():
+                continue
+            if (flavor, p.name) in SKIP_PACKAGES:
+                continue
+            dirs.append(p)
+    return dirs
+
+
+@pytest.mark.parametrize(
+    "package_dir",
+    _package_dirs(),
+    ids=lambda p: f"{p.parent.name}/{p.name}",
+)
+def test_readme_exists(package_dir: Path):
+    """Each generated SDK package folder (azure & unbranded) must contain a README.md."""
+    readme_path = package_dir / "README.md"
+    assert readme_path.is_file(), f"README.md not found at {readme_path}"