diff --git a/.github/workflows/d-day-labeler.yml b/.github/workflows/d-day-labeler.yml
new file mode 100644
index 000000000..355664e3d
--- /dev/null
+++ b/.github/workflows/d-day-labeler.yml
@@ -0,0 +1,100 @@
+name: Update D-n Labels
+
+on:
+  schedule:
+    - cron: '0 0 * * *' # UTC 00:00 = KST 09:00
+
+permissions:
+  contents: read
+  pull-requests: write
+
+jobs:
+  d-day-labeler:
+    runs-on: ubuntu-latest
+
+    steps:
+      # Step A: 업데이트 전 상태 스냅샷
+      - name: Snapshot BEFORE d-day update
+        id: before
+        uses: actions/github-script@v7
+        with:
+          script: |
+            const pulls = await github.rest.pulls.list({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              state: "open",
+              base: "dev"
+            });
+
+            const before = {};
+            for (const pr of pulls.data) {
+              const d = pr.labels.find(l => /^D-\d+$/.test(l.name));
+              if (d) before[pr.number] = d.name;
+            }
+
+            return before;
+
+      # Step B: D-n 라벨 업데이트
+      - name: Update D-n Labels
+        uses: naver/d-day-labeler@latest
+        with:
+          token: ${{ secrets.GITHUB_TOKEN }}
+
+      # Step C: 업데이트 후 상태 + diff 판단
+      - name: Detect D-2→D-1 / D-1→D-0
+        id: detect
+        uses: actions/github-script@v7
+        with:
+          script: |
+            const before = JSON.parse(`${{ steps.before.outputs.result }}`);
+
+            const pulls = await github.rest.pulls.list({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              state: "open",
+              base: "dev"
+            });
+
+            const notify = [];
+
+            for (const pr of pulls.data) {
+              const afterLabel = pr.labels.find(l => /^D-\d+$/.test(l.name));
+              if (!afterLabel) continue;
+
+              const after = afterLabel.name;
+              const prev = before[pr.number];
+
+              if (
+                (prev === "D-2" && after === "D-1") ||
+                (prev === "D-1" && after === "D-0")
+              ) {
+                notify.push({
+                  number: pr.number,
+                  title: pr.title,
+                  url: pr.html_url,
+                  prefix: after === "D-0" ? "🚨 [D-0]" : "⏳ [D-1]"
+                });
+              }
+            }
+
+            return notify;
+
+      # Discord 알림
+      - name: Send Discord notification
+        if: ${{ steps.detect.outputs.result != '[]' }}
+        env:
+          DISCORD_WEBHOOK_URL: ${{ secrets.DISCORD_PR_REMINDER_WEBHOOK_URL }}
+        run: |
+          content=$(echo '${{ steps.detect.outputs.result }}' | jq -r '
+            .[] |
+            (.prefix + " PR #" + (.number|tostring) + ": " + .title) + "\n" + .url + "\n"
+          ')
+
+          jq -n \
+            --arg title "⏰ 마감 임박 PR 알림" \
+            --arg body "$content" \
+            '{content: ($title + "\n\n" + $body)}' \
+          | curl -X POST \
+              -H "Content-Type: application/json" \
+              -d @- \
+              "$DISCORD_WEBHOOK_URL"
diff --git a/.github/workflows/simple-labeler.yml b/.github/workflows/simple-labeler.yml
new file mode 100644
index 000000000..524c74494
--- /dev/null
+++ b/.github/workflows/simple-labeler.yml
@@ -0,0 +1,21 @@
+name: Simple Labeler
+
+on:
+  pull_request:
+    types: [opened, ready_for_review]
+    branches:
+      - dev
+
+permissions:
+  pull-requests: write
+
+jobs:
+  simple-labeler:
+    runs-on: [ubuntu-latest]
+    steps:
+      - name: Label to PR
+        uses: naver/simple-labeler@latest
+        with:
+          token: ${{ secrets.GITHUB_TOKEN }}
+          labels: "D-4"
+          duplicate: "D-*"