diff --git a/.github/workflows/sync_roadmap_status.yml b/.github/workflows/sync_roadmap_status.yml
index 5194817..0acc23f 100644
--- a/.github/workflows/sync_roadmap_status.yml
+++ b/.github/workflows/sync_roadmap_status.yml
@@ -9,12 +9,19 @@ on:
   # (already in the event payload) and write to ROADMAP.md on main.
   pull_request_target:
     types: [opened, ready_for_review, closed]
+  # Run reconcile.py on demand ("Run workflow" button) and once a day
+  # as a safety net against any missed event (e.g. an issue closed
+  # before its ROADMAP.md line had "— #N" linked to it yet).
+  workflow_dispatch: {}
+  schedule:
+    - cron: "0 4 * * *"
 
 permissions:
   contents: write
 
 jobs:
   sync:
+    if: github.event_name == 'issues' || github.event_name == 'pull_request_target'
     runs-on: ubuntu-latest
     steps:
       - uses: actions/checkout@v4
@@ -39,6 +46,39 @@ jobs:
           commit_message: "chore: sync roadmap status [skip ci]"
           file_pattern: ROADMAP.md
 
+      - name: Sync Discord
+        if: steps.update.outputs.changed == 'true'
+        run: python scripts/roadmap/sync_discord.py
+        env:
+          DISCORD_WEBHOOK_URL: ${{ secrets.DISCORD_WEBHOOK_URL }}
+          DISCORD_MESSAGE_IDS: ${{ vars.DISCORD_MESSAGE_IDS }}
+
+  reconcile:
+    if: github.event_name == 'workflow_dispatch' || github.event_name == 'schedule'
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v4
+        with:
+          ref: main
+
+      - uses: actions/setup-python@v5
+        with:
+          python-version: "3.12"
+
+      - name: Reconcile ROADMAP.md with issue states
+        id: update
+        run: python scripts/roadmap/reconcile_roadmap.py
+        env:
+          GITHUB_REPOSITORY: ${{ github.repository }}
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+
+      - name: Commit ROADMAP.md
+        if: steps.update.outputs.changed == 'true'
+        uses: stefanzweifel/git-auto-commit-action@v5
+        with:
+          commit_message: "chore: reconcile roadmap status [skip ci]"
+          file_pattern: ROADMAP.md
+
       - name: Sync Discord
         if: steps.update.outputs.changed == 'true'
         run: python scripts/roadmap/sync_discord.py
diff --git a/ROADMAP.md b/ROADMAP.md
index 5ade97d..a948ae0 100644
--- a/ROADMAP.md
+++ b/ROADMAP.md
@@ -10,7 +10,7 @@ This may be subject to change.
 1. Introduction
     * [x] How course works?
     * [x] Motivation and Mindset
-    * [ ] Asking for Help (WIP) — #32
+    * [ ] Asking for Help — #32
     * [ ] Join the Community — #33
     * [x] Computer Science basics, Programming and Python 
 2. Prerequisites 
diff --git a/scripts/roadmap/reconcile_roadmap.py b/scripts/roadmap/reconcile_roadmap.py
new file mode 100644
index 0000000..930994e
--- /dev/null
+++ b/scripts/roadmap/reconcile_roadmap.py
@@ -0,0 +1,96 @@
+#!/usr/bin/env python3
+"""
+Scans every issue already linked in ROADMAP.md ("— #N") and sets its
+checkbox to match that issue's CURRENT state on GitHub — closed,
+assigned, or neither.
+
+Use this:
+  - once, right after linking a batch of issues, to catch anything that
+    changed *before* the link existed — sync_roadmap.py only reacts to
+    events on lines that already have "— #N" on them, so a PR merged
+    before you added the link is invisible to it
+  - on a schedule, as a safety net in case a future event is ever missed
+    (a failed workflow run, a webhook delivery hiccup, etc.)
+
+Unlike sync_roadmap.py, this doesn't look at PR state directly — an
+issue's own state (closed / has an assignee) is used as the signal.
+That covers the common paths (assigned, merged-and-closed) even for
+history that predates the automation.
+"""
+
+import json
+import os
+import sys
+import urllib.error
+import urllib.request
+
+sys.path.insert(0, os.path.dirname(__file__))
+from sync_roadmap import LINE_RE, ROADMAP_PATH, apply_updates  # noqa: E402
+
+
+def find_linked_issues() -> set[int]:
+    with open(ROADMAP_PATH, encoding="utf-8") as f:
+        lines = f.readlines()
+
+    issues = set()
+    for line in lines:
+        m = LINE_RE.match(line.rstrip("\n"))
+        if m:
+            issues.add(int(m.group("issue")))
+    return issues
+
+
+def fetch_issue(repo: str, token: str, number: int) -> dict:
+    url = f"https://api.github.com/repos/{repo}/issues/{number}"
+    req = urllib.request.Request(
+        url,
+        headers={
+            "Authorization": f"Bearer {token}",
+            "Accept": "application/vnd.github+json",
+        },
+    )
+    with urllib.request.urlopen(req) as resp:
+        return json.load(resp)
+
+
+def target_state(issue: dict) -> str:
+    if issue.get("state") == "closed":
+        return "x"
+    if issue.get("assignees"):
+        return "-"
+    return " "
+
+
+def main() -> None:
+    repo = os.environ["GITHUB_REPOSITORY"]
+    token = os.environ["GITHUB_TOKEN"]
+
+    issue_numbers = find_linked_issues()
+    if not issue_numbers:
+        print("No linked issues found in ROADMAP.md.")
+        return
+
+    updates: dict[int, str] = {}
+    for number in sorted(issue_numbers):
+        try:
+            issue = fetch_issue(repo, token, number)
+        except urllib.error.HTTPError as e:
+            print(
+                f"#{number}: could not fetch issue ({e.code}) — skipping",
+                file=sys.stderr,
+            )
+            continue
+        updates[number] = target_state(issue)
+
+    changed = apply_updates(updates)
+    if not changed:
+        print("Roadmap already matched issue states.")
+
+    github_output = os.environ.get("GITHUB_OUTPUT")
+    if github_output:
+        with open(github_output, "a", encoding="utf-8") as f:
+            f.write(f"changed={'true' if changed else 'false'}\n")
+
+
+if __name__ == "__main__":
+    main()