diff --git a/site/Makefile b/site/Makefile
index d46f551947..d944db545f 100644
--- a/site/Makefile
+++ b/site/Makefile
@@ -326,6 +326,8 @@ notebooks:
 	@rm -rf $(DEST_DIR_NB)/templates
 	@echo "Copying _metadata.yml into notebooks/ ..."
 	@cp developer/_metadata.yml $(DEST_DIR_NB)/_metadata.yml
+	@echo "Updating developer/_sidebar.yaml with code_samples directories ..."
+	@python scripts/update_code_samples_sidebar.py
 	@echo "Zip up notebooks.zip ..."
 	@zip -r notebooks.zip $(DEST_DIR_NB) > /dev/null 2>&1
 
diff --git a/site/developer/_sidebar.yaml b/site/developer/_sidebar.yaml
index 3cbeea5b45..3b1680ea69 100644
--- a/site/developer/_sidebar.yaml
+++ b/site/developer/_sidebar.yaml
@@ -53,7 +53,27 @@ website:
         - text: "Notebooks"
         - text: "Code samples"
           file: developer/samples-jupyter-notebooks.qmd
-          contents: "notebooks/code_samples/**"
+          contents:
+            - section: "Agents"
+              contents: "notebooks/code_samples/agents/**"
+            - section: "Capital markets"
+              contents: "notebooks/code_samples/capital_markets/**"
+            - section: "Code explainer"
+              contents: "notebooks/code_samples/code_explainer/**"
+            - section: "Credit risk"
+              contents: "notebooks/code_samples/credit_risk/**"
+            - section: "Custom tests"
+              contents: "notebooks/code_samples/custom_tests/**"
+            - section: "Model validation"
+              contents: "notebooks/code_samples/model_validation/**"
+            - section: "NLP and LLM"
+              contents: "notebooks/code_samples/nlp_and_llm/**"
+            - section: "Ongoing monitoring"
+              contents: "notebooks/code_samples/ongoing_monitoring/**"
+            - section: "Regression"
+              contents: "notebooks/code_samples/regression/**"
+            - section: "Time series"
+              contents: "notebooks/code_samples/time_series/**"
         - text: "---"
         - text: "Reference"
         - text: "{{< var validmind.api >}}"
diff --git a/site/scripts/update_code_samples_sidebar.py b/site/scripts/update_code_samples_sidebar.py
new file mode 100644
index 0000000000..c9d31fa5d3
--- /dev/null
+++ b/site/scripts/update_code_samples_sidebar.py
@@ -0,0 +1,94 @@
+# Copyright © 2023-2026 ValidMind Inc. All rights reserved.
+# Refer to the LICENSE file in the root of this repository for details.
+# SPDX-License-Identifier: AGPL-3.0 AND ValidMind Commercial
+"""
+Update developer/_sidebar.yaml so the Code samples entry lists each
+subdirectory of notebooks/code_samples/ explicitly (with wildcards),
+in alphabetical order, with fixed capitalization for NLP and LLM.
+
+Run from the site/ directory, e.g.:
+    cd site && python scripts/update_code_samples_sidebar.py
+"""
+
+import os
+from pathlib import Path
+
+
+# Display title for directories that need fixed capitalization (e.g. acronyms)
+SPECIAL_TITLES = {
+    "nlp_and_llm": "NLP and LLM",
+}
+
+
+def dir_to_title(dirname: str) -> str:
+    """Convert directory name to sidebar display title (sentence-style capitalization)."""
+    if dirname in SPECIAL_TITLES:
+        return SPECIAL_TITLES[dirname]
+    return dirname.replace("_", " ").capitalize()
+
+
+def main() -> None:
+    # Run from site/ or repo root
+    cwd = Path.cwd()
+    if (cwd / "notebooks" / "code_samples").is_dir():
+        base = cwd
+    elif (cwd / "site" / "notebooks" / "code_samples").is_dir():
+        base = cwd / "site"
+    else:
+        raise SystemExit("Run from site/ or repo root (e.g. cd site && python scripts/update_code_samples_sidebar.py)")
+    code_samples = base / "notebooks" / "code_samples"
+    sidebar_path = base / "developer" / "_sidebar.yaml"
+
+    if not code_samples.is_dir():
+        raise SystemExit(f"Directory not found: {code_samples}")
+    if not sidebar_path.is_file():
+        raise SystemExit(f"Sidebar file not found: {sidebar_path}")
+
+    subdirs = sorted(
+        d for d in os.listdir(code_samples)
+        if (code_samples / d).is_dir()
+    )
+
+    # Build the new contents block (YAML). Use "section" so Quarto renders
+    # expandable accordion items; "text" alone does not expand.
+    lines = [
+        '          contents:',
+    ]
+    for d in subdirs:
+        title = dir_to_title(d)
+        lines.append(f'            - section: "{title}"')
+        lines.append(f'              contents: "notebooks/code_samples/{d}/**"')
+
+    new_block = "\n".join(lines)
+
+    text = sidebar_path.read_text()
+    # Replace either the single wildcard or an existing expanded block
+    old_single = '          contents: "notebooks/code_samples/**"'
+    if old_single in text:
+        text = text.replace(old_single, new_block, 1)
+    else:
+        # Find the code_samples contents block and replace it (multi-line)
+        import re
+        # Match from "          contents:" through all following lines that are
+        # "            - ..." or "              contents: ..." for code_samples
+        pattern = re.compile(
+            r'(        - text: "Code samples"\n'
+            r'          file: developer/samples-jupyter-notebooks\.qmd\n)'
+            r'          contents:\n'
+            r'(            - (?:text|section): "[^"]+"\n'
+            r'              contents: "notebooks/code_samples/[^"]+\*\*"\n)*',
+            re.MULTILINE,
+        )
+        match = pattern.search(text)
+        if not match:
+            raise SystemExit(
+                "Could not find Code samples contents block in sidebar. "
+                "Has the sidebar format changed?"
+            )
+        text = text[: match.start()] + match.group(1) + new_block + "\n" + text[match.end() :]
+    sidebar_path.write_text(text)
+    print(f"Updated {sidebar_path} with {len(subdirs)} code sample directories.")
+
+
+if __name__ == "__main__":
+    main()