diff --git a/.github/workflows/cleanup-pr-tarballs.yml b/.github/workflows/cleanup-pr-tarballs.yml
index 1892f3a17..10a35be2c 100644
--- a/.github/workflows/cleanup-pr-tarballs.yml
+++ b/.github/workflows/cleanup-pr-tarballs.yml
@@ -14,10 +14,16 @@ jobs:
     runs-on: ubuntu-latest
 
     steps:
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
       - uses: actions/checkout@v6
       - name: Delete PR tarball releases older than 7 days
         env:
-          GH_TOKEN: ${{ github.token }}
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
         run: |
           CUTOFF=$(date -u -d '7 days ago' +%Y-%m-%dT%H:%M:%SZ 2>/dev/null || date -u -v-7d +%Y-%m-%dT%H:%M:%SZ)
 
diff --git a/.github/workflows/pr-tarball.yml b/.github/workflows/pr-tarball.yml
index a901a2a6e..269530868 100644
--- a/.github/workflows/pr-tarball.yml
+++ b/.github/workflows/pr-tarball.yml
@@ -50,10 +50,16 @@ jobs:
         run: |
           TARBALL_NAME=$(ls *.tgz | head -1 | xargs basename)
           echo "name=$TARBALL_NAME" >> $GITHUB_OUTPUT
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
       - name: Create or update PR release
         id: release
         env:
-          GH_TOKEN: ${{ github.token }}
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
           PR_NUMBER: ${{ github.event.pull_request.number }}
           TARBALL_NAME: ${{ steps.tarball.outputs.name }}
         run: |
diff --git a/.github/workflows/release-main-and-preview.yml b/.github/workflows/release-main-and-preview.yml
index b3cfb5ee2..c726518f2 100644
--- a/.github/workflows/release-main-and-preview.yml
+++ b/.github/workflows/release-main-and-preview.yml
@@ -135,9 +135,16 @@ jobs:
       - name: Update snapshots
         run: npm run test:update-snapshots
 
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
+
       - name: Create release branch and PR
         env:
-          GH_TOKEN: ${{ github.token }}
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
           NEW_VERSION: ${{ steps.bump.outputs.version }}
         run: |
           BRANCH_NAME="release/v$NEW_VERSION"
@@ -219,9 +226,16 @@ jobs:
       - name: Update snapshots
         run: npm run test:update-snapshots
 
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
+
       - name: Create release branch and PR
         env:
-          GH_TOKEN: ${{ github.token }}
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
           NEW_VERSION: ${{ steps.bump.outputs.version }}
         run: |
           BRANCH_NAME="release/v$NEW_VERSION"
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 394e9460a..8a0713162 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -160,9 +160,16 @@ jobs:
             exit 1
           fi
 
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
+
       - name: Create Pull Request
         env:
-          GH_TOKEN: ${{ github.token }}
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
           NEW_VERSION: ${{ steps.bump.outputs.version }}
           BASE_BRANCH: ${{ steps.release-meta.outputs.base_branch }}
           DIST_TAG: ${{ steps.release-meta.outputs.dist_tag }}
diff --git a/.github/workflows/strands-command.yml b/.github/workflows/strands-command.yml
index a4e20a16b..dcf768206 100644
--- a/.github/workflows/strands-command.yml
+++ b/.github/workflows/strands-command.yml
@@ -94,6 +94,12 @@ jobs:
             };
             await processInputs(context, github, core, inputs);
 
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
       - name: Run Strands Agent
         uses: ./.github/actions/strands-action
         with:
@@ -104,7 +110,7 @@ jobs:
           tools: 'strands_tools:shell,retrieve'
           aws_role_arn: ${{ secrets.AWS_ROLE_ARN }}
           aws_region: 'us-west-2'
-          pat_token: ${{ secrets.GITHUB_TOKEN }}
+          pat_token: ${{ steps.app-token.outputs.token }}
         env:
           SESSION_ID: ${{ steps.process-inputs.outputs.session_id }}
           S3_SESSION_BUCKET: ${{ secrets.AGENT_SESSIONS_BUCKET }}
diff --git a/.github/workflows/sync-from-public.yml b/.github/workflows/sync-from-public.yml
index b0b6ed106..e38a4d625 100644
--- a/.github/workflows/sync-from-public.yml
+++ b/.github/workflows/sync-from-public.yml
@@ -13,10 +13,17 @@ jobs:
   sync:
     runs-on: ubuntu-latest
     steps:
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
+
       - uses: actions/checkout@v4
         with:
           fetch-depth: 0
-          token: ${{ secrets.GITHUB_TOKEN }}
+          token: ${{ steps.app-token.outputs.token }}
 
       - name: Configure Git
         run: |
@@ -101,15 +108,22 @@ jobs:
               --head "$conflict_branch" || echo "⚠️  Failed to create PR"
           fi
         env:
-          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
 
   sync-preview:
     runs-on: ubuntu-latest
     steps:
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
+
       - uses: actions/checkout@v4
         with:
           fetch-depth: 0
-          token: ${{ secrets.GITHUB_TOKEN }}
+          token: ${{ steps.app-token.outputs.token }}
 
       - name: Configure Git
         run: |
@@ -194,4 +208,4 @@ jobs:
               --head "$conflict_branch" || echo "⚠️  Failed to create PR"
           fi
         env:
-          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
diff --git a/.github/workflows/sync-preview.yml b/.github/workflows/sync-preview.yml
index 61abcbc86..b4f0fa1b0 100644
--- a/.github/workflows/sync-preview.yml
+++ b/.github/workflows/sync-preview.yml
@@ -17,19 +17,27 @@ jobs:
     name: Merge main into preview
     runs-on: ubuntu-latest
     steps:
+      - name: Generate GitHub App Token
+        id: app-token
+        uses: actions/create-github-app-token@v1
+        with:
+          app-id: ${{ vars.APP_ID }}
+          private-key: ${{ secrets.APP_PRIVATE_KEY }}
+
       - name: Checkout preview
         uses: actions/checkout@v6
         with:
           ref: preview
           fetch-depth: 0
+          token: ${{ steps.app-token.outputs.token }}
 
       - name: Configure git
         run: |
           git config --global user.name "github-actions[bot]"
           git config --global user.email "github-actions[bot]@users.noreply.github.com"
 
-      - name: Merge main into preview
-        id: merge
+      - name: Check if sync needed
+        id: check
         run: |
           git fetch origin main
           MAIN_SHA=$(git rev-parse origin/main)
@@ -37,73 +45,133 @@ jobs:
 
           if [[ "$MAIN_SHA" == "$MERGE_BASE" ]]; then
             echo "✅ preview already contains all of main"
-            echo "status=up-to-date" >> $GITHUB_OUTPUT
-            exit 0
+            echo "needed=false" >> $GITHUB_OUTPUT
+          else
+            echo "needed=true" >> $GITHUB_OUTPUT
           fi
 
-          echo "ℹ️  Merging main into preview..."
+      - name: Skip if already synced
+        if: steps.check.outputs.needed == 'false'
+        run: echo "Nothing to sync."
+
+      - name: Merge main into preview
+        if: steps.check.outputs.needed == 'true'
+        id: merge
+        run: |
+          # Save preview's version before merge so we can restore it after
+          PREVIEW_VERSION=$(node -p "require('./package.json').version")
+          echo "preview_version=$PREVIEW_VERSION" >> $GITHUB_OUTPUT
 
           if git merge origin/main --no-edit -m "chore: merge main into preview"; then
-            git push origin preview
-            echo "✅ main merged into preview and pushed"
-            echo "status=merged" >> $GITHUB_OUTPUT
+            echo "status=clean" >> $GITHUB_OUTPUT
           else
-            git merge --abort
-            echo "status=conflict" >> $GITHUB_OUTPUT
+            # preview carries a higher version string than main (e.g. 1.0.0-preview.X vs 0.13.X).
+            # This means package.json/package-lock.json almost always conflict on the version field.
+            # Accept main's content here; the version is restored in the next step.
+            for f in package.json package-lock.json; do
+              if git diff --name-only --diff-filter=U | grep -qx "$f"; then
+                git checkout --theirs "$f"
+                git add "$f"
+                echo "  ↳ resolved $f conflict (accepted main, will restore version)"
+              fi
+            done
+
+            # Check if all conflicts are now resolved
+            if [[ -z "$(git diff --name-only --diff-filter=U)" ]]; then
+              git commit --no-edit -m "chore: merge main into preview"
+              echo "status=clean" >> $GITHUB_OUTPUT
+            else
+              echo "status=conflict" >> $GITHUB_OUTPUT
+            fi
           fi
 
-      - name: Get original commit author
-        if: steps.merge.outputs.status == 'conflict'
-        id: author
+      - name: Restore preview-owned files
+        if: steps.merge.outputs.status == 'clean'
         run: |
-          AUTHOR=$(git log origin/main -1 --format='%an')
-          GH_USER=$(git log origin/main -1 --format='%ae' | grep -oP '.*(?=@users\.noreply\.github\.com)' || echo "")
-          if [[ -z "$GH_USER" ]]; then
-            # Try to get GitHub username from the commit
-            GH_USER=$(gh api "/repos/${{ github.repository }}/commits/$(git rev-parse origin/main)" --jq '.author.login // empty' 2>/dev/null || echo "")
+          # These files are auto-generated during preview releases and must not
+          # be overwritten by main's versions (schema-check CI will reject changes
+          # to schemas/, and CHANGELOG.md tracks preview releases separately).
+          PREVIEW_HEAD=$(git rev-parse HEAD^1)
+          for f in schemas/agentcore.schema.v1.json CHANGELOG.md; do
+            if git show "$PREVIEW_HEAD:$f" > /dev/null 2>&1; then
+              git show "$PREVIEW_HEAD:$f" > "$f"
+              git add "$f"
+              echo "  ↳ restored preview's $f"
+            fi
+          done
+          if ! git diff --cached --quiet; then
+            git commit -m "chore: restore preview-owned files (schema, changelog)"
           fi
-          echo "name=$AUTHOR" >> $GITHUB_OUTPUT
-          echo "gh_user=$GH_USER" >> $GITHUB_OUTPUT
-        env:
-          GH_TOKEN: ${{ github.token }}
+
+      - name: Restore preview version and push
+        if: steps.merge.outputs.status == 'clean'
+        run: |
+          PREVIEW_VERSION="${{ steps.merge.outputs.preview_version }}"
+          CURRENT_VERSION=$(node -p "require('./package.json').version")
+
+          if [[ "$CURRENT_VERSION" != "$PREVIEW_VERSION" ]]; then
+            PREVIEW_VERSION="$PREVIEW_VERSION" node -e "
+              const fs = require('fs');
+              const pkg = JSON.parse(fs.readFileSync('package.json', 'utf8'));
+              pkg.version = process.env.PREVIEW_VERSION;
+              fs.writeFileSync('package.json', JSON.stringify(pkg, null, 2) + '\n');
+            "
+            if [[ -f package-lock.json ]]; then
+              PREVIEW_VERSION="$PREVIEW_VERSION" node -e "
+                const fs = require('fs');
+                const lock = JSON.parse(fs.readFileSync('package-lock.json', 'utf8'));
+                lock.version = process.env.PREVIEW_VERSION;
+                if (lock.packages && lock.packages['']) {
+                  lock.packages[''].version = process.env.PREVIEW_VERSION;
+                }
+                fs.writeFileSync('package-lock.json', JSON.stringify(lock, null, 2) + '\n');
+              "
+            fi
+            git add package.json
+            [[ -f package-lock.json ]] && git add package-lock.json
+            git commit -m "chore: restore preview version ($PREVIEW_VERSION)"
+          fi
+
+          git push origin HEAD:preview
+          echo "✅ main merged into preview and pushed"
 
       - name: Create PR for conflict resolution
         if: steps.merge.outputs.status == 'conflict'
         env:
-          GH_TOKEN: ${{ github.token }}
-          AUTHOR_NAME: ${{ steps.author.outputs.name }}
-          AUTHOR_GH: ${{ steps.author.outputs.gh_user }}
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
         run: |
-          BRANCH="sync-preview/merge-main-$(date +%Y%m%d-%H%M%S)"
-
-          # Check if there's already an open sync PR
-          EXISTING=$(gh pr list --base preview --search "sync-preview: merge main into preview" --state open --json number --jq 'length')
-          if [[ "$EXISTING" != "0" ]]; then
+          # Check if there's already an open sync PR (match by branch prefix, not title search)
+          COUNT=$(gh pr list --base preview --state open --json headRefName \
+            --jq '[.[] | select(.headRefName | startswith("sync-preview/"))] | length')
+          if [[ "$COUNT" != "0" ]]; then
             echo "ℹ️  Sync PR already open — skipping duplicate."
             exit 0
           fi
 
-          # Create a branch from preview with the conflict markers
+          # Abort the failed merge and redo on a branch for the PR
+          git merge --abort
+
+          BRANCH="sync-preview/merge-main-$(date +%Y%m%d-%H%M%S)"
           git checkout -b "$BRANCH"
-          git merge origin/main --no-edit -m "chore: merge main into preview" || true
+          git merge origin/main --no-edit -m "chore: merge main into preview (conflicts need resolution)" || true
           git add -A
           git commit --no-edit -m "chore: merge main into preview (conflicts need resolution)" || true
           git push origin "$BRANCH"
 
-          # Build mention string
+          GH_USER=$(gh api "/repos/${{ github.repository }}/commits/$(git rev-parse origin/main)" --jq '.author.login // empty' 2>/dev/null || echo "")
           MENTION=""
-          if [[ -n "$AUTHOR_GH" ]]; then
-            MENTION="cc @${AUTHOR_GH}"
+          if [[ -n "$GH_USER" ]]; then
+            MENTION="cc @${GH_USER}"
           fi
 
           gh pr create \
             --base preview \
             --head "$BRANCH" \
-            --title "sync-preview: merge main into preview" \
+            --title "sync-preview: merge main into preview (conflicts)" \
             --body "$(cat <<BODY
-          The automated sync-preview workflow could not cleanly merge \`main\` into \`preview\`.
+          The automated sync could not cleanly merge \`main\` into \`preview\`.
 
-          **This PR contains the merge with conflict markers.** To resolve:
+          **This PR contains conflict markers.** To resolve:
 
           1. Check out this branch locally:
              \`\`\`bash
@@ -116,8 +184,6 @@ jobs:
           3. Keep preview-specific values (package version, preview tests, etc.) — accept main's changes for everything else.
           4. Commit and push, then merge this PR.
 
-          This must be resolved before the next coordinated release.
-
           ${MENTION}
 
           _Opened automatically by the sync-preview workflow._
diff --git a/package-lock.json b/package-lock.json
index dbff7fe37..96fa23e72 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -15,7 +15,7 @@
         "@aws-sdk/client-bedrock": "^3.1012.0",
         "@aws-sdk/client-bedrock-agent": "^3.1012.0",
         "@aws-sdk/client-bedrock-agentcore": "^3.1020.0",
-        "@aws-sdk/client-bedrock-agentcore-control": "^3.1020.0",
+        "@aws-sdk/client-bedrock-agentcore-control": "^3.1039.0",
         "@aws-sdk/client-bedrock-runtime": "^3.893.0",
         "@aws-sdk/client-cloudformation": "^3.893.0",
         "@aws-sdk/client-cloudwatch-logs": "^3.893.0",
@@ -27,7 +27,7 @@
         "@aws/agent-inspector": "0.3.0",
         "@commander-js/extra-typings": "^14.0.0",
         "@opentelemetry/api": "^1.9.1",
-        "@opentelemetry/exporter-metrics-otlp-http": "^0.217.0",
+        "@opentelemetry/exporter-metrics-otlp-http": "^0.215.0",
         "@opentelemetry/otlp-transformer": "^0.213.0",
         "@opentelemetry/resources": "^2.6.1",
         "@opentelemetry/sdk-metrics": "^2.6.1",
@@ -77,7 +77,7 @@
         "lint-staged": "^16.2.7",
         "node-pty": "^1.1.0",
         "prettier": "^3.7.4",
-        "secretlint": "^13.0.0",
+        "secretlint": "^12.2.0",
         "tsx": "^4.21.0",
         "typescript": "^5",
         "typescript-eslint": "^8.50.1",
@@ -242,9 +242,9 @@
       }
     },
     "node_modules/@aws-cdk/cloud-assembly-schema": {
-      "version": "53.19.0",
-      "resolved": "https://registry.npmjs.org/@aws-cdk/cloud-assembly-schema/-/cloud-assembly-schema-53.19.0.tgz",
-      "integrity": "sha512-pHtEeuiPwYu4vWJhqTqBCvOWy2w4BjYFW5W8L5lH5AzhKLLG92o+Ck0oLcKUkB0Ucl4ff49WL9K7sa7g35ionw==",
+      "version": "53.18.0",
+      "resolved": "https://registry.npmjs.org/@aws-cdk/cloud-assembly-schema/-/cloud-assembly-schema-53.18.0.tgz",
+      "integrity": "sha512-/fa6rOpokkfa5tVIdhsaexQq5MVVTSsZSD1Tu45YcrdyGRusGrM9RlPMCPrwvMS1UfdVFBhcgO9dl9ODWAWOeQ==",
       "bundleDependencies": [
         "jsonschema",
         "semver"
@@ -377,14 +377,14 @@
       }
     },
     "node_modules/@aws-cdk/toolkit-lib": {
-      "version": "1.25.0",
-      "resolved": "https://registry.npmjs.org/@aws-cdk/toolkit-lib/-/toolkit-lib-1.25.0.tgz",
-      "integrity": "sha512-yTxQLcI7T8wfUAhWw8vO7dG//x0WL786AA5u4i/yRtSVSJd+0frHX6gD+njSv41OaNLhwP6EVYkFz9wTyCt64A==",
+      "version": "1.24.0",
+      "resolved": "https://registry.npmjs.org/@aws-cdk/toolkit-lib/-/toolkit-lib-1.24.0.tgz",
+      "integrity": "sha512-tgtH0CJ8/N/CpT1/ebOBfUpxdAMSRsP9LTAjWfa+E0clX4Vuvx0w1J1bGYwtvKY9nQUbFIO4QfgNEHz8hVlMUA==",
       "license": "Apache-2.0",
       "dependencies": {
         "@aws-cdk/cdk-assets-lib": "^1",
         "@aws-cdk/cloud-assembly-api": "2.2.2",
-        "@aws-cdk/cloud-assembly-schema": ">=53.19.0",
+        "@aws-cdk/cloud-assembly-schema": ">=53.18.0",
         "@aws-cdk/cloudformation-diff": "^2",
         "@aws-cdk/cx-api": "^2",
         "@aws-sdk/client-appsync": "^3",
@@ -415,7 +415,7 @@
         "@smithy/util-retry": "^4",
         "@smithy/util-waiter": "^4",
         "archiver": "^7.0.1",
-        "cdk-from-cfn": "^0.297.0",
+        "cdk-from-cfn": "^0.295.0",
         "chalk": "^4",
         "chokidar": "^4",
         "fast-deep-equal": "^3.1.3",
@@ -687,24 +687,24 @@
       }
     },
     "node_modules/@aws-sdk/client-application-signals": {
-      "version": "3.1038.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/client-application-signals/-/client-application-signals-3.1038.0.tgz",
-      "integrity": "sha512-kUBaXESTxZO+JiMQIFU/Wv0Lop+KtuJP0xOv00dL/4a0RdcqNdAwbH7RnxXaL5z7toDLCfg9j93f0IQEdBLbXA==",
+      "version": "3.1037.0",
+      "resolved": "https://registry.npmjs.org/@aws-sdk/client-application-signals/-/client-application-signals-3.1037.0.tgz",
+      "integrity": "sha512-xnGVyIWU1SXNSnnARvU3U3sic0QWH0wek/X3WpXFCpOm0NBzbTablWiAszNDU9RCvg9KUDm6Wdp0T4jnodXhEg==",
       "license": "Apache-2.0",
       "dependencies": {
         "@aws-crypto/sha256-browser": "5.2.0",
         "@aws-crypto/sha256-js": "5.2.0",
-        "@aws-sdk/core": "^3.974.6",
-        "@aws-sdk/credential-provider-node": "^3.972.37",
+        "@aws-sdk/core": "^3.974.5",
+        "@aws-sdk/credential-provider-node": "^3.972.36",
         "@aws-sdk/middleware-host-header": "^3.972.10",
         "@aws-sdk/middleware-logger": "^3.972.10",
         "@aws-sdk/middleware-recursion-detection": "^3.972.11",
-        "@aws-sdk/middleware-user-agent": "^3.972.36",
+        "@aws-sdk/middleware-user-agent": "^3.972.35",
         "@aws-sdk/region-config-resolver": "^3.972.13",
         "@aws-sdk/types": "^3.973.8",
         "@aws-sdk/util-endpoints": "^3.996.8",
         "@aws-sdk/util-user-agent-browser": "^3.972.10",
-        "@aws-sdk/util-user-agent-node": "^3.973.22",
+        "@aws-sdk/util-user-agent-node": "^3.973.21",
         "@smithy/config-resolver": "^4.4.17",
         "@smithy/core": "^3.23.17",
         "@smithy/fetch-http-handler": "^5.3.17",
@@ -712,7 +712,7 @@
         "@smithy/invalid-dependency": "^4.2.14",
         "@smithy/middleware-content-length": "^4.2.14",
         "@smithy/middleware-endpoint": "^4.4.32",
-        "@smithy/middleware-retry": "^4.5.6",
+        "@smithy/middleware-retry": "^4.5.5",
         "@smithy/middleware-serde": "^4.2.20",
         "@smithy/middleware-stack": "^4.2.14",
         "@smithy/node-config-provider": "^4.3.14",
@@ -728,7 +728,7 @@
         "@smithy/util-defaults-mode-node": "^4.2.54",
         "@smithy/util-endpoints": "^3.4.2",
         "@smithy/util-middleware": "^4.2.14",
-        "@smithy/util-retry": "^4.3.5",
+        "@smithy/util-retry": "^4.3.4",
         "@smithy/util-utf8": "^4.2.2",
         "tslib": "^2.6.2"
       },
@@ -788,25 +788,25 @@
       }
     },
     "node_modules/@aws-sdk/client-bedrock": {
-      "version": "3.1038.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/client-bedrock/-/client-bedrock-3.1038.0.tgz",
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@@ -1051,6 +1051,42 @@
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@@ -1154,24 +1190,24 @@
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+        "@sindresorhus/merge-streams": "^4.0.0",
+        "fast-glob": "^3.3.3",
+        "ignore": "^7.0.5",
+        "is-path-inside": "^4.0.0",
+        "slash": "^5.1.0",
+        "unicorn-magic": "^0.4.0"
+      },
+      "engines": {
+        "node": ">=20"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
     "node_modules/gopd": {
       "version": "1.2.0",
       "resolved": "https://registry.npmjs.org/gopd/-/gopd-1.2.0.tgz",
@@ -10764,6 +10914,19 @@
         "url": "https://github.com/sponsors/ljharb"
       }
     },
+    "node_modules/is-path-inside": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/is-path-inside/-/is-path-inside-4.0.0.tgz",
+      "integrity": "sha512-lJJV/5dYS+RcL8uQdBDW9c9uWFLLBNRyFhnAKXw5tVqLlKZ4RMGZKv+YQ/IA3OhD+RpbJa1LLFM1FQPGyIXvOA==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=12"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
     "node_modules/is-plain-obj": {
       "version": "4.1.0",
       "resolved": "https://registry.npmjs.org/is-plain-obj/-/is-plain-obj-4.1.0.tgz",
@@ -13377,9 +13540,9 @@
       }
     },
     "node_modules/path-scurry/node_modules/lru-cache": {
-      "version": "11.3.5",
-      "resolved": "https://registry.npmjs.org/lru-cache/-/lru-cache-11.3.5.tgz",
-      "integrity": "sha512-NxVFwLAnrd9i7KUBxC4DrUhmgjzOs+1Qm50D3oF1/oL+r1NpZ4gA7xvG0/zJ8evR7zIKn4vLf7qTNduWFtCrRw==",
+      "version": "11.3.6",
+      "resolved": "https://registry.npmjs.org/lru-cache/-/lru-cache-11.3.6.tgz",
+      "integrity": "sha512-Gf/KoL3C/MlI7Bt0PGI9I+TeTC/I6r/csU58N4BSNc4lppLBeKsOdFYkK+dX0ABDUMJNfCHTyPpzwwO21Awd3A==",
       "license": "BlueOak-1.0.0",
       "engines": {
         "node": "20 || >=22"
@@ -13711,9 +13874,9 @@
       }
     },
     "node_modules/react": {
-      "version": "19.2.6",
-      "resolved": "https://registry.npmjs.org/react/-/react-19.2.6.tgz",
-      "integrity": "sha512-sfWGGfavi0xr8Pg0sVsyHMAOziVYKgPLNrS7ig+ivMNb3wbCBw3KxtflsGBAwD3gYQlE/AEZsTLgToRrSCjb0Q==",
+      "version": "19.2.5",
+      "resolved": "https://registry.npmjs.org/react/-/react-19.2.5.tgz",
+      "integrity": "sha512-llUJLzz1zTUBrskt2pwZgLq59AemifIftw4aB7JxOqf1HY2FDaGDxgwpAPVzHU1kdWabH7FauP4i1oEeer2WCA==",
       "license": "MIT",
       "engines": {
         "node": ">=0.10.0"
@@ -14236,19 +14399,19 @@
       "license": "MIT"
     },
     "node_modules/secretlint": {
-      "version": "13.0.0",
-      "resolved": "https://registry.npmjs.org/secretlint/-/secretlint-13.0.0.tgz",
-      "integrity": "sha512-bc4dzeaYMiuorNAb4cPoOX87gb+w0kiReZaUEx9iu8u0/PrkMj5QCm6pXji/NDc4Z6HUZO5ihfd0HY/4iPzskQ==",
+      "version": "12.3.1",
+      "resolved": "https://registry.npmjs.org/secretlint/-/secretlint-12.3.1.tgz",
+      "integrity": "sha512-wv8TKCjU5hbBxo5jKEX8wIE78VAoL0Ux7pu18+TxtbICMZ2OCbu6EmO3OJLbUbyfUXSPVryNLNmGVgvwY6Z0xw==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
-        "@secretlint/config-creator": "13.0.0",
-        "@secretlint/formatter": "13.0.0",
-        "@secretlint/node": "13.0.0",
-        "@secretlint/profiler": "13.0.0",
-        "@secretlint/resolver": "13.0.0",
-        "@secretlint/walker": "13.0.0",
+        "@secretlint/config-creator": "12.3.1",
+        "@secretlint/formatter": "12.3.1",
+        "@secretlint/node": "12.3.1",
+        "@secretlint/profiler": "12.3.1",
+        "@secretlint/resolver": "12.3.1",
         "debug": "^4.4.3",
+        "globby": "^16.2.0",
         "read-pkg": "^10.1.0"
       },
       "bin": {
@@ -14483,6 +14646,19 @@
         "url": "https://github.com/sponsors/isaacs"
       }
     },
+    "node_modules/slash": {
+      "version": "5.1.0",
+      "resolved": "https://registry.npmjs.org/slash/-/slash-5.1.0.tgz",
+      "integrity": "sha512-ZA6oR3T/pEyuqwMgAKT0/hAv8oAXckzbkmR0UkUosQ+Mc4RxGoJkRmwHgHufaenlyAgE1Mxgpdcrf75y6XcnDg==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=14.16"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
     "node_modules/slice-ansi": {
       "version": "8.0.0",
       "resolved": "https://registry.npmjs.org/slice-ansi/-/slice-ansi-8.0.0.tgz",
diff --git a/package.json b/package.json
index 2516faaab..5f040158e 100644
--- a/package.json
+++ b/package.json
@@ -78,7 +78,7 @@
     "@aws-sdk/client-bedrock": "^3.1012.0",
     "@aws-sdk/client-bedrock-agent": "^3.1012.0",
     "@aws-sdk/client-bedrock-agentcore": "^3.1020.0",
-    "@aws-sdk/client-bedrock-agentcore-control": "^3.1020.0",
+    "@aws-sdk/client-bedrock-agentcore-control": "^3.1039.0",
     "@aws-sdk/client-bedrock-runtime": "^3.893.0",
     "@aws-sdk/client-cloudformation": "^3.893.0",
     "@aws-sdk/client-cloudwatch-logs": "^3.893.0",
@@ -90,7 +90,7 @@
     "@aws/agent-inspector": "0.3.0",
     "@commander-js/extra-typings": "^14.0.0",
     "@opentelemetry/api": "^1.9.1",
-    "@opentelemetry/exporter-metrics-otlp-http": "^0.217.0",
+    "@opentelemetry/exporter-metrics-otlp-http": "^0.215.0",
     "@opentelemetry/otlp-transformer": "^0.213.0",
     "@opentelemetry/resources": "^2.6.1",
     "@opentelemetry/sdk-metrics": "^2.6.1",
@@ -141,7 +141,7 @@
     "lint-staged": "^16.2.7",
     "node-pty": "^1.1.0",
     "prettier": "^3.7.4",
-    "secretlint": "^13.0.0",
+    "secretlint": "^12.2.0",
     "tsx": "^4.21.0",
     "typescript": "^5",
     "typescript-eslint": "^8.50.1",
diff --git a/src/cli/aws/agentcore-control.ts b/src/cli/aws/agentcore-control.ts
index d2770bacf..8a8569cf0 100644
--- a/src/cli/aws/agentcore-control.ts
+++ b/src/cli/aws/agentcore-control.ts
@@ -469,6 +469,7 @@ export interface GetEvaluatorResult {
     llmAsAJudge?: GetEvaluatorLlmConfig;
     codeBased?: GetEvaluatorCodeBasedConfig;
   };
+  kmsKeyArn?: string;
   tags?: Record<string, string>;
 }
 
@@ -547,6 +548,7 @@ export async function getEvaluator(options: GetEvaluatorOptions): Promise<GetEva
     status: response.status ?? 'UNKNOWN',
     description: response.description,
     evaluatorConfig,
+    kmsKeyArn: response.kmsKeyArn,
     tags,
   };
 }
diff --git a/src/cli/commands/deploy/__tests__/utils.test.ts b/src/cli/commands/deploy/__tests__/utils.test.ts
new file mode 100644
index 000000000..8bf07311a
--- /dev/null
+++ b/src/cli/commands/deploy/__tests__/utils.test.ts
@@ -0,0 +1,54 @@
+import type { AgentCoreProjectSpec } from '../../../../schema';
+import { computeDeployAttrs } from '../utils.js';
+import { describe, expect, it } from 'vitest';
+
+describe('computeDeployAttrs', () => {
+  it('computes counts from a populated spec', () => {
+    const projectSpec = {
+      runtimes: [{}, {}],
+      memories: [{}],
+      credentials: [{}, {}, {}],
+      evaluators: [{}],
+      onlineEvalConfigs: [{}, {}],
+      agentCoreGateways: [{ targets: [{}, {}] }, { targets: [{}] }],
+      policyEngines: [{ policies: [{}, {}] }, { policies: [{}] }],
+    } as unknown as Partial<AgentCoreProjectSpec>;
+
+    expect(computeDeployAttrs(projectSpec, 'diff')).toEqual({
+      runtime_count: 2,
+      memory_count: 1,
+      credential_count: 3,
+      evaluator_count: 1,
+      online_eval_count: 2,
+      gateway_count: 2,
+      gateway_target_count: 3,
+      policy_engine_count: 2,
+      policy_count: 3,
+      mode: 'diff',
+    });
+  });
+
+  it('returns zeros for empty spec', () => {
+    expect(computeDeployAttrs({}, 'deploy')).toEqual({
+      runtime_count: 0,
+      memory_count: 0,
+      credential_count: 0,
+      evaluator_count: 0,
+      online_eval_count: 0,
+      gateway_count: 0,
+      gateway_target_count: 0,
+      policy_engine_count: 0,
+      policy_count: 0,
+      mode: 'deploy',
+    });
+  });
+
+  it('handles dry-run mode', () => {
+    const projectSpec = { runtimes: [{}] } as unknown as Partial<AgentCoreProjectSpec>;
+    const attrs = computeDeployAttrs(projectSpec, 'dry-run');
+
+    expect(attrs.runtime_count).toBe(1);
+    expect(attrs.memory_count).toBe(0);
+    expect(attrs.mode).toBe('dry-run');
+  });
+});
diff --git a/src/cli/commands/deploy/command.tsx b/src/cli/commands/deploy/command.tsx
index fc235ac51..8126cfce4 100644
--- a/src/cli/commands/deploy/command.tsx
+++ b/src/cli/commands/deploy/command.tsx
@@ -1,15 +1,19 @@
+import { ConfigIO } from '../../../lib';
 import { getErrorMessage } from '../../errors';
+import { withCommandRunTelemetry } from '../../telemetry/cli-command-run.js';
 import { COMMAND_DESCRIPTIONS } from '../../tui/copy';
 import { requireProject, requireTTY } from '../../tui/guards';
 import { DeployScreen } from '../../tui/screens/deploy/DeployScreen';
 import { handleDeploy } from './actions';
-import { createSpinnerProgress } from './progress';
-import type { DeployOptions } from './types';
+import type { DeployOptions, DeployResult } from './types';
+import { DEFAULT_DEPLOY_ATTRS, computeDeployAttrs } from './utils';
 import { validateDeployOptions } from './validate';
 import type { Command } from '@commander-js/extra-typings';
 import { Text, render } from 'ink';
 import React from 'react';
 
+const SPINNER_FRAMES = ['⠋', '⠙', '⠹', '⠸', '⠼', '⠴', '⠦', '⠧', '⠇', '⠏'];
+
 function handleDeployTUI(options: { autoConfirm?: boolean; diffMode?: boolean } = {}): void {
   requireProject();
 
@@ -37,8 +41,69 @@ async function handleDeployCLI(options: DeployOptions): Promise<void> {
     process.exit(1);
   }
 
-  const progressUtil = options.progress ? createSpinnerProgress() : undefined;
-  const onProgress = progressUtil?.onProgress;
+  // Compute attrs upfront from project spec (available before deploy)
+  const mode = options.diff ? 'diff' : options.plan ? 'dry-run' : 'deploy';
+  const attrs = await new ConfigIO()
+    .readProjectSpec()
+    .then(spec => computeDeployAttrs(spec, mode))
+    .catch(() => ({ ...DEFAULT_DEPLOY_ATTRS, mode }) as const);
+
+  const { deployResult } = await withCommandRunTelemetry('deploy', attrs, async () => {
+    const result = await executeDeploy(options).catch(
+      (e): DeployResult => ({ success: false, error: getErrorMessage(e) })
+    );
+    if (!result.success) {
+      return { success: false as const, error: result.error ?? 'Deploy failed', deployResult: result };
+    }
+    return { success: true as const, deployResult: result };
+  });
+
+  // ALL output happens here, after telemetry
+  if (!deployResult.success) {
+    if (options.json) {
+      console.log(JSON.stringify(deployResult));
+    } else {
+      console.error(deployResult.error);
+      if (deployResult.logPath) {
+        console.error(`Log: ${deployResult.logPath}`);
+      }
+    }
+    process.exit(1);
+  }
+
+  printDeployResult(deployResult as DeployResult & { success: true }, options);
+
+  if (deployResult.postDeployWarnings && deployResult.postDeployWarnings.length > 0) {
+    process.exit(2);
+  }
+  process.exit(0);
+}
+
+async function executeDeploy(options: DeployOptions): Promise<DeployResult> {
+  let spinner: NodeJS.Timeout | undefined;
+
+  // Progress callback for --progress mode
+  const onProgress = options.progress
+    ? (step: string, status: 'start' | 'success' | 'error') => {
+        if (spinner) {
+          clearInterval(spinner);
+          process.stdout.write('\r\x1b[K'); // Clear line
+        }
+
+        if (status === 'start') {
+          let i = 0;
+          process.stdout.write(`${SPINNER_FRAMES[0]} ${step}...`);
+          spinner = setInterval(() => {
+            i = (i + 1) % SPINNER_FRAMES.length;
+            process.stdout.write(`\r${SPINNER_FRAMES[i]} ${step}...`);
+          }, 80);
+        } else if (status === 'success') {
+          console.log(`✓ ${step}`);
+        } else {
+          console.log(`✗ ${step}`);
+        }
+      }
+    : undefined;
 
   const onResourceEvent = options.verbose
     ? (message: string) => {
@@ -56,57 +121,57 @@ async function handleDeployCLI(options: DeployOptions): Promise<void> {
     onResourceEvent,
   });
 
-  progressUtil?.cleanup();
+  if (spinner) {
+    clearInterval(spinner);
+    process.stdout.write('\r\x1b[K');
+  }
+
+  return result;
+}
 
+function printDeployResult(result: DeployResult & { success: true }, options: DeployOptions): void {
   if (options.json) {
     console.log(JSON.stringify(result));
-  } else if (result.success) {
-    if (options.diff) {
-      console.log(`\n✓ Diff complete for '${result.targetName}' (stack: ${result.stackName})`);
-    } else if (options.plan) {
-      console.log(`\n✓ Dry run complete for '${result.targetName}' (stack: ${result.stackName})`);
-      console.log('\nRun `agentcore deploy` to deploy.');
-    } else {
-      console.log(`\n✓ Deployed to '${result.targetName}' (stack: ${result.stackName})`);
+    return;
+  }
 
-      // Show stack outputs in non-JSON mode
-      if (result.outputs && Object.keys(result.outputs).length > 0) {
-        console.log('\nOutputs:');
-        for (const [key, value] of Object.entries(result.outputs)) {
-          console.log(`  ${key}: ${value}`);
-        }
-      }
+  if (options.diff) {
+    console.log(`\n✓ Diff complete for '${result.targetName}' (stack: ${result.stackName})`);
+  } else if (options.plan) {
+    console.log(`\n✓ Dry run complete for '${result.targetName}' (stack: ${result.stackName})`);
+    console.log('\nRun `agentcore deploy` to deploy.');
+  } else {
+    console.log(`\n✓ Deployed to '${result.targetName}' (stack: ${result.stackName})`);
 
-      if (result.postDeployWarnings && result.postDeployWarnings.length > 0) {
-        console.log('\n⚠ Post-deploy warnings:');
-        for (const warning of result.postDeployWarnings) {
-          console.log(`  ${warning}`);
-        }
+    // Show stack outputs in non-JSON mode
+    if (result.outputs && Object.keys(result.outputs).length > 0) {
+      console.log('\nOutputs:');
+      for (const [key, value] of Object.entries(result.outputs)) {
+        console.log(`  ${key}: ${value}`);
       }
+    }
 
-      if (result.notes && result.notes.length > 0) {
-        for (const note of result.notes) {
-          console.log(`\nNote: ${note}`);
-        }
+    if (result.postDeployWarnings && result.postDeployWarnings.length > 0) {
+      console.log('\n⚠ Post-deploy warnings:');
+      for (const warning of result.postDeployWarnings) {
+        console.log(`  ${warning}`);
       }
+    }
 
-      if (result.nextSteps && result.nextSteps.length > 0) {
-        console.log(`Next: ${result.nextSteps.join(' | ')}`);
+    if (result.notes && result.notes.length > 0) {
+      for (const note of result.notes) {
+        console.log(`\nNote: ${note}`);
       }
     }
 
-    if (result.logPath) {
-      console.log(`\nLog: ${result.logPath}`);
-    }
-  } else {
-    console.error(result.error);
-    if (result.logPath) {
-      console.error(`Log: ${result.logPath}`);
+    if (result.nextSteps && result.nextSteps.length > 0) {
+      console.log(`Next: ${result.nextSteps.join(' | ')}`);
     }
   }
 
-  const hasPostDeployWarnings = result.success && result.postDeployWarnings && result.postDeployWarnings.length > 0;
-  process.exit(result.success ? (hasPostDeployWarnings ? 2 : 0) : 1);
+  if (result.logPath) {
+    console.log(`\nLog: ${result.logPath}`);
+  }
 }
 
 export const registerDeploy = (program: Command) => {
diff --git a/src/cli/commands/deploy/utils.ts b/src/cli/commands/deploy/utils.ts
new file mode 100644
index 000000000..d0db1ec08
--- /dev/null
+++ b/src/cli/commands/deploy/utils.ts
@@ -0,0 +1,33 @@
+import type { AgentCoreProjectSpec } from '../../../schema';
+
+export type DeployMode = 'deploy' | 'dry-run' | 'diff';
+
+export const DEFAULT_DEPLOY_ATTRS = {
+  runtime_count: 0,
+  memory_count: 0,
+  credential_count: 0,
+  evaluator_count: 0,
+  online_eval_count: 0,
+  gateway_count: 0,
+  gateway_target_count: 0,
+  policy_engine_count: 0,
+  policy_count: 0,
+  mode: 'deploy' as DeployMode,
+};
+
+export function computeDeployAttrs(projectSpec: Partial<AgentCoreProjectSpec>, mode: DeployMode) {
+  const gateways = projectSpec.agentCoreGateways ?? [];
+  const policyEngines = projectSpec.policyEngines ?? [];
+  return {
+    runtime_count: (projectSpec.runtimes ?? []).length,
+    memory_count: (projectSpec.memories ?? []).length,
+    credential_count: (projectSpec.credentials ?? []).length,
+    evaluator_count: (projectSpec.evaluators ?? []).length,
+    online_eval_count: (projectSpec.onlineEvalConfigs ?? []).length,
+    gateway_count: gateways.length,
+    gateway_target_count: gateways.reduce((sum, g) => sum + (g.targets ?? []).length, 0),
+    policy_engine_count: policyEngines.length,
+    policy_count: policyEngines.reduce((sum, pe) => sum + (pe.policies ?? []).length, 0),
+    mode,
+  };
+}
diff --git a/src/cli/commands/import/__tests__/import-evaluator.test.ts b/src/cli/commands/import/__tests__/import-evaluator.test.ts
index 5e6fb5e96..1795ce4fe 100644
--- a/src/cli/commands/import/__tests__/import-evaluator.test.ts
+++ b/src/cli/commands/import/__tests__/import-evaluator.test.ts
@@ -210,6 +210,49 @@ describe('toEvaluatorSpec', () => {
 
     expect(result.tags).toBeUndefined();
   });
+
+  it('forwards kmsKeyArn when present', () => {
+    const detail: GetEvaluatorResult = {
+      evaluatorId: 'eval-kms',
+      evaluatorArn: 'arn:aws:bedrock-agentcore:us-west-2:123456789012:evaluator/eval-kms',
+      evaluatorName: 'kms_eval',
+      level: 'SESSION',
+      status: 'ACTIVE',
+      evaluatorConfig: {
+        llmAsAJudge: {
+          model: 'anthropic.claude-3-5-sonnet-20241022-v2:0',
+          instructions: 'Evaluate',
+          ratingScale: { numerical: [{ value: 1, label: 'Low', definition: 'Low' }] },
+        },
+      },
+      kmsKeyArn: 'arn:aws:kms:us-west-2:123456789012:key/12345678-1234-1234-1234-123456789012',
+    };
+
+    const result = toEvaluatorSpec(detail, 'kms_eval');
+
+    expect(result.kmsKeyArn).toBe('arn:aws:kms:us-west-2:123456789012:key/12345678-1234-1234-1234-123456789012');
+  });
+
+  it('omits kmsKeyArn when not present', () => {
+    const detail: GetEvaluatorResult = {
+      evaluatorId: 'eval-no-kms',
+      evaluatorArn: 'arn:aws:bedrock-agentcore:us-west-2:123456789012:evaluator/eval-no-kms',
+      evaluatorName: 'no_kms_eval',
+      level: 'SESSION',
+      status: 'ACTIVE',
+      evaluatorConfig: {
+        llmAsAJudge: {
+          model: 'anthropic.claude-3-5-sonnet-20241022-v2:0',
+          instructions: 'Evaluate',
+          ratingScale: { numerical: [{ value: 1, label: 'Low', definition: 'Low' }] },
+        },
+      },
+    };
+
+    const result = toEvaluatorSpec(detail, 'no_kms_eval');
+
+    expect(result.kmsKeyArn).toBeUndefined();
+  });
 });
 
 // ============================================================================
diff --git a/src/cli/commands/import/import-evaluator.ts b/src/cli/commands/import/import-evaluator.ts
index 7c6c8b0d2..447f1316c 100644
--- a/src/cli/commands/import/import-evaluator.ts
+++ b/src/cli/commands/import/import-evaluator.ts
@@ -50,6 +50,7 @@ export function toEvaluatorSpec(detail: GetEvaluatorResult, localName: string):
     level,
     ...(detail.description && { description: detail.description }),
     config,
+    ...(detail.kmsKeyArn && { kmsKeyArn: detail.kmsKeyArn }),
     ...(detail.tags && Object.keys(detail.tags).length > 0 && { tags: detail.tags }),
   };
 }
diff --git a/src/cli/primitives/EvaluatorPrimitive.ts b/src/cli/primitives/EvaluatorPrimitive.ts
index ed255c061..d9f972fa7 100644
--- a/src/cli/primitives/EvaluatorPrimitive.ts
+++ b/src/cli/primitives/EvaluatorPrimitive.ts
@@ -1,6 +1,6 @@
 import { findConfigRoot } from '../../lib';
 import type { EvaluationLevel, Evaluator, EvaluatorConfig } from '../../schema';
-import { EvaluationLevelSchema, EvaluatorSchema } from '../../schema';
+import { EvaluationLevelSchema, EvaluatorSchema, isValidKmsKeyArn } from '../../schema';
 import { getErrorMessage } from '../errors';
 import type { RemovalPreview, RemovalResult, SchemaChange } from '../operations/remove/types';
 import { runCliCommand } from '../telemetry/cli-command-run.js';
@@ -25,6 +25,7 @@ export interface AddEvaluatorOptions {
   level: EvaluationLevel;
   description?: string;
   config: EvaluatorConfig;
+  kmsKeyArn?: string;
 }
 
 export type RemovableEvaluator = RemovableResource;
@@ -184,6 +185,7 @@ export class EvaluatorPrimitive extends BasePrimitive<AddEvaluatorOptions, Remov
         '--config <path>',
         'Path to evaluator config JSON file (overrides --model, --instructions, --rating-scale) [non-interactive]'
       )
+      .option('--kms-key-arn <arn>', 'KMS key ARN for evaluator encryption (optional)')
       .option('--json', 'Output as JSON [non-interactive]')
       .action(
         async (cliOptions: {
@@ -196,6 +198,7 @@ export class EvaluatorPrimitive extends BasePrimitive<AddEvaluatorOptions, Remov
           lambdaArn?: string;
           timeout?: string;
           config?: string;
+          kmsKeyArn?: string;
           json?: boolean;
         }) => {
           if (!findConfigRoot()) {
@@ -289,10 +292,17 @@ export class EvaluatorPrimitive extends BasePrimitive<AddEvaluatorOptions, Remov
                 };
               }
 
+              if (cliOptions.kmsKeyArn && !isValidKmsKeyArn(cliOptions.kmsKeyArn)) {
+                fail(
+                  '--kms-key-arn must be a valid KMS key ARN (e.g. arn:aws:kms:us-east-1:123456789012:key/12345678-1234-1234-1234-123456789012)'
+                );
+              }
+
               const result = await this.add({
                 name: cliOptions.name!,
                 level: levelResult.data!,
                 config: configJson,
+                kmsKeyArn: cliOptions.kmsKeyArn,
               });
 
               if (!result.success) {
@@ -386,6 +396,7 @@ export class EvaluatorPrimitive extends BasePrimitive<AddEvaluatorOptions, Remov
       level: options.level,
       ...(options.description && { description: options.description }),
       config: options.config,
+      ...(options.kmsKeyArn && { kmsKeyArn: options.kmsKeyArn }),
     };
 
     project.evaluators.push(evaluator);
diff --git a/src/cli/telemetry/schemas/__tests__/command-run.test.ts b/src/cli/telemetry/schemas/__tests__/command-run.test.ts
index 110df1284..2df12d271 100644
--- a/src/cli/telemetry/schemas/__tests__/command-run.test.ts
+++ b/src/cli/telemetry/schemas/__tests__/command-run.test.ts
@@ -47,7 +47,7 @@ describe('COMMAND_SCHEMAS', () => {
       gateway_target_count: 3,
       policy_engine_count: 0,
       policy_count: 0,
-      has_diff: true,
+      mode: 'diff',
     };
     expect(COMMAND_SCHEMAS.deploy.parse(attrs)).toEqual(attrs);
   });
@@ -64,7 +64,7 @@ describe('COMMAND_SCHEMAS', () => {
         gateway_target_count: 0,
         policy_engine_count: 0,
         policy_count: 0,
-        has_diff: false,
+        mode: 'deploy',
       })
     ).toThrow();
   });
@@ -81,7 +81,7 @@ describe('COMMAND_SCHEMAS', () => {
         gateway_target_count: 0,
         policy_engine_count: 0,
         policy_count: 0,
-        has_diff: false,
+        mode: 'deploy',
       })
     ).toThrow();
   });
diff --git a/src/cli/telemetry/schemas/command-run.ts b/src/cli/telemetry/schemas/command-run.ts
index 6386e297d..bf79f42eb 100644
--- a/src/cli/telemetry/schemas/command-run.ts
+++ b/src/cli/telemetry/schemas/command-run.ts
@@ -100,7 +100,7 @@ const DeployAttrs = safeSchema({
   gateway_target_count: Count,
   policy_engine_count: Count,
   policy_count: Count,
-  has_diff: z.boolean(),
+  mode: z.enum(['deploy', 'dry-run', 'diff']),
 });
 
 const DevAttrs = safeSchema({
diff --git a/src/cli/tui/hooks/useCreateEvaluator.ts b/src/cli/tui/hooks/useCreateEvaluator.ts
index 087eca479..5336cdc82 100644
--- a/src/cli/tui/hooks/useCreateEvaluator.ts
+++ b/src/cli/tui/hooks/useCreateEvaluator.ts
@@ -8,6 +8,7 @@ interface CreateEvaluatorConfig {
   name: string;
   level: string;
   config: EvaluatorConfig;
+  kmsKeyArn?: string;
 }
 
 export function useCreateEvaluator() {
@@ -29,6 +30,7 @@ export function useCreateEvaluator() {
             name: config.name,
             level: config.level as 'SESSION' | 'TRACE' | 'TOOL_CALL',
             config: config.config,
+            kmsKeyArn: config.kmsKeyArn,
           })
       );
       if (!addResult.success) {
diff --git a/src/cli/tui/screens/deploy/useDeployFlow.ts b/src/cli/tui/screens/deploy/useDeployFlow.ts
index 33531e521..5d77a5543 100644
--- a/src/cli/tui/screens/deploy/useDeployFlow.ts
+++ b/src/cli/tui/screens/deploy/useDeployFlow.ts
@@ -12,6 +12,7 @@ import {
   parsePolicyEngineOutputs,
   parsePolicyOutputs,
 } from '../../../cloudformation';
+import { DEFAULT_DEPLOY_ATTRS, computeDeployAttrs } from '../../../commands/deploy/utils.js';
 import { getErrorMessage, isChangesetInProgressError, isExpiredTokenError } from '../../../errors';
 import { ExecLogger } from '../../../logging';
 import { performStackTeardown, setupTransactionSearch } from '../../../operations/deploy';
@@ -24,6 +25,7 @@ import {
 } from '../../../operations/deploy/post-deploy-config-bundles';
 import { setupHttpGateways } from '../../../operations/deploy/post-deploy-http-gateways';
 import { enableOnlineEvalConfigs } from '../../../operations/deploy/post-deploy-online-evals';
+import { type OperationResult, withCommandRunTelemetry } from '../../../telemetry/cli-command-run.js';
 import {
   type StackDiffSummary,
   type Step,
@@ -603,7 +605,9 @@ export function useDeployFlow(options: DeployFlowOptions = {}): DeployFlowState
     if (deployStep.status !== 'pending') return;
     if (!cdkToolkitWrapper) return;
 
-    const run = async () => {
+    const attrs = context ? computeDeployAttrs(context.projectSpec, 'deploy') : { ...DEFAULT_DEPLOY_ATTRS };
+
+    const run = async (): Promise<OperationResult> => {
       // Run diff before deploy to capture pre-deploy differences
       if (!isDiffRunningRef.current) {
         isDiffRunningRef.current = true;
@@ -751,6 +755,7 @@ export function useDeployFlow(options: DeployFlowOptions = {}): DeployFlowState
         // Mark both steps as success (in case CFn events were never received)
         setPublishAssetsStep(prev => ({ ...prev, status: 'success' }));
         setDeployStep(prev => ({ ...prev, status: 'success' }));
+        return { success: true } as const;
       } catch (err) {
         const errorMsg = getErrorMessage(err);
 
@@ -782,6 +787,7 @@ export function useDeployFlow(options: DeployFlowOptions = {}): DeployFlowState
             error: logger.getFailureMessage('Publish assets'),
           }));
         }
+        return { success: false, error: errorMsg };
       } finally {
         // Disable verbose output and clear callback after deploy
         switchableIoHost?.setVerbose(false);
@@ -791,7 +797,7 @@ export function useDeployFlow(options: DeployFlowOptions = {}): DeployFlowState
       }
     };
 
-    void run();
+    void withCommandRunTelemetry('deploy', attrs, run);
   }, [
     preflight.phase,
     cdkToolkitWrapper,
@@ -816,7 +822,11 @@ export function useDeployFlow(options: DeployFlowOptions = {}): DeployFlowState
     if (diffStep.status !== 'pending') return;
     if (!cdkToolkitWrapper) return;
 
-    const run = async () => {
+    const attrs = context
+      ? computeDeployAttrs(context.projectSpec, 'diff')
+      : { ...DEFAULT_DEPLOY_ATTRS, mode: 'diff' as const };
+
+    const run = async (): Promise<OperationResult> => {
       setDiffStep(prev => ({ ...prev, status: 'running' }));
       setShouldStartDeploy(false);
       setDiffSummaries([]);
@@ -837,6 +847,7 @@ export function useDeployFlow(options: DeployFlowOptions = {}): DeployFlowState
         logger.endStep('success');
         logger.finalize(true);
         setDiffStep(prev => ({ ...prev, status: 'success' }));
+        return { success: true };
       } catch (err) {
         const errorMsg = getErrorMessage(err);
         logger.endStep('error', errorMsg);
@@ -851,6 +862,7 @@ export function useDeployFlow(options: DeployFlowOptions = {}): DeployFlowState
           status: 'error',
           error: logger.getFailureMessage('Run CDK diff'),
         }));
+        return { success: false, error: errorMsg };
       } finally {
         switchableIoHost?.setVerbose(false);
         switchableIoHost?.setOnRawMessage(null);
@@ -858,7 +870,7 @@ export function useDeployFlow(options: DeployFlowOptions = {}): DeployFlowState
       }
     };
 
-    void run();
+    void withCommandRunTelemetry('deploy', attrs, run);
   }, [
     diffMode,
     preflight.phase,
diff --git a/src/cli/tui/screens/evaluator/AddEvaluatorScreen.tsx b/src/cli/tui/screens/evaluator/AddEvaluatorScreen.tsx
index 2c4a2f465..b4294f978 100644
--- a/src/cli/tui/screens/evaluator/AddEvaluatorScreen.tsx
+++ b/src/cli/tui/screens/evaluator/AddEvaluatorScreen.tsx
@@ -1,5 +1,5 @@
 import type { EvaluationLevel, EvaluatorConfig } from '../../../../schema';
-import { EvaluatorNameSchema, isValidBedrockModelId } from '../../../../schema';
+import { EvaluatorNameSchema, isValidBedrockModelId, isValidKmsKeyArn } from '../../../../schema';
 import type { SelectableItem } from '../../components';
 import { ConfirmReview, Panel, Screen, StepIndicator, TextInput, WizardSelect } from '../../components';
 import { HELP_TEXT } from '../../constants';
@@ -91,6 +91,7 @@ export function AddEvaluatorScreen({ onComplete, onExit, existingEvaluatorNames
   const isRatingScaleCustomStep = wizard.step === 'ratingScale-custom';
   const isLambdaArnStep = wizard.step === 'lambda-arn';
   const isTimeoutStep = wizard.step === 'timeout';
+  const isKmsKeyArnStep = wizard.step === 'kms-key-arn';
   const isConfirmStep = wizard.step === 'confirm';
 
   const evaluatorTypeNav = useListNavigation({
@@ -163,6 +164,8 @@ export function AddEvaluatorScreen({ onComplete, onExit, existingEvaluatorNames
 
   // Build confirm fields based on evaluator type
   const confirmFields = useMemo(() => {
+    const kmsField = wizard.config.kmsKeyArn ? [{ label: 'KMS Key ARN', value: wizard.config.kmsKeyArn }] : [];
+
     if (wizard.evaluatorType === 'llm-as-a-judge') {
       const llm = wizard.config.config.llmAsAJudge!;
       return [
@@ -175,6 +178,7 @@ export function AddEvaluatorScreen({ onComplete, onExit, existingEvaluatorNames
           value: llm.instructions.length > 60 ? llm.instructions.slice(0, 60) + '...' : llm.instructions,
         },
         { label: 'Rating Scale', value: formatRatingScale(llm.ratingScale) },
+        ...kmsField,
       ];
     }
 
@@ -187,6 +191,7 @@ export function AddEvaluatorScreen({ onComplete, onExit, existingEvaluatorNames
         { label: 'Code', value: managed.codeLocation },
         { label: 'Entrypoint', value: managed.entrypoint },
         { label: 'Timeout', value: `${managed.timeoutSeconds}s` },
+        ...kmsField,
       ];
     }
 
@@ -197,6 +202,7 @@ export function AddEvaluatorScreen({ onComplete, onExit, existingEvaluatorNames
       { label: 'Name', value: wizard.config.name },
       { label: 'Level', value: wizard.config.level },
       { label: 'Lambda ARN', value: external.lambdaArn },
+      ...kmsField,
     ];
   }, [wizard.evaluatorType, wizard.codeBasedType, wizard.config]);
 
@@ -374,6 +380,21 @@ export function AddEvaluatorScreen({ onComplete, onExit, existingEvaluatorNames
           />
         )}
 
+        {isKmsKeyArnStep && (
+          <TextInput
+            key="kms-key-arn"
+            prompt="KMS key ARN for encryption (optional, press Enter to skip)"
+            initialValue=""
+            onSubmit={wizard.setKmsKeyArn}
+            onCancel={() => wizard.goBack()}
+            customValidation={value =>
+              value === '' ||
+              isValidKmsKeyArn(value) ||
+              'Must be a valid KMS key ARN (e.g. arn:aws:kms:us-east-1:123456789012:key/12345678-1234-1234-1234-123456789012)'
+            }
+          />
+        )}
+
         {isConfirmStep && <ConfirmReview fields={confirmFields} />}
       </Panel>
     </Screen>
diff --git a/src/cli/tui/screens/evaluator/types.ts b/src/cli/tui/screens/evaluator/types.ts
index 4b19bf85d..229e8b8d5 100644
--- a/src/cli/tui/screens/evaluator/types.ts
+++ b/src/cli/tui/screens/evaluator/types.ts
@@ -20,12 +20,14 @@ export type AddEvaluatorStep =
   | 'ratingScale-custom'
   | 'lambda-arn'
   | 'timeout'
+  | 'kms-key-arn'
   | 'confirm';
 
 export interface AddEvaluatorConfig {
   name: string;
   level: EvaluationLevel;
   config: EvaluatorConfig;
+  kmsKeyArn?: string;
 }
 
 export const EVALUATOR_STEP_LABELS: Record<AddEvaluatorStep, string> = {
@@ -41,6 +43,7 @@ export const EVALUATOR_STEP_LABELS: Record<AddEvaluatorStep, string> = {
   'ratingScale-custom': 'Scale',
   'lambda-arn': 'Lambda',
   timeout: 'Timeout',
+  'kms-key-arn': 'KMS Key',
   confirm: 'Confirm',
 };
 
diff --git a/src/cli/tui/screens/evaluator/useAddEvaluatorWizard.ts b/src/cli/tui/screens/evaluator/useAddEvaluatorWizard.ts
index 1bc54f50b..ff31f2009 100644
--- a/src/cli/tui/screens/evaluator/useAddEvaluatorWizard.ts
+++ b/src/cli/tui/screens/evaluator/useAddEvaluatorWizard.ts
@@ -22,6 +22,7 @@ const LLM_STEPS: AddEvaluatorStep[] = [
   'model',
   'instructions',
   'ratingScale',
+  'kms-key-arn',
   'confirm',
 ];
 const CODE_MANAGED_STEPS: AddEvaluatorStep[] = [
@@ -30,6 +31,7 @@ const CODE_MANAGED_STEPS: AddEvaluatorStep[] = [
   'name',
   'level',
   'timeout',
+  'kms-key-arn',
   'confirm',
 ];
 const CODE_EXTERNAL_STEPS: AddEvaluatorStep[] = [
@@ -38,6 +40,7 @@ const CODE_EXTERNAL_STEPS: AddEvaluatorStep[] = [
   'name',
   'level',
   'lambda-arn',
+  'kms-key-arn',
   'confirm',
 ];
 
@@ -80,6 +83,7 @@ export function useAddEvaluatorWizard() {
   const [lambdaArn, setLambdaArnState] = useState('');
   const [timeout, setTimeoutState] = useState(DEFAULT_CODE_TIMEOUT);
   const [customRatingScaleType, setCustomRatingScaleType] = useState<CustomRatingScaleType>('numerical');
+  const [kmsKeyArn, setKmsKeyArnState] = useState('');
   const [step, setStep] = useState<AddEvaluatorStep>('evaluator-type');
 
   const steps = useMemo(() => getSteps(evaluatorType, codeBasedType), [evaluatorType, codeBasedType]);
@@ -109,11 +113,13 @@ export function useAddEvaluatorWizard() {
 
   // Build the final config based on current state
   const config: AddEvaluatorConfig = useMemo(() => {
+    const kms = kmsKeyArn || undefined;
     if (evaluatorType === 'llm-as-a-judge') {
       return {
         name,
         level,
         config: { llmAsAJudge: llmConfig },
+        ...(kms && { kmsKeyArn: kms }),
       };
     }
 
@@ -126,6 +132,7 @@ export function useAddEvaluatorWizard() {
             external: { lambdaArn },
           },
         },
+        ...(kms && { kmsKeyArn: kms }),
       };
     }
 
@@ -143,8 +150,9 @@ export function useAddEvaluatorWizard() {
           },
         },
       },
+      ...(kms && { kmsKeyArn: kms }),
     };
-  }, [evaluatorType, codeBasedType, name, level, llmConfig, lambdaArn, timeout]);
+  }, [evaluatorType, codeBasedType, name, level, llmConfig, lambdaArn, timeout, kmsKeyArn]);
 
   const selectEvaluatorType = useCallback((type: EvaluatorTypeId) => {
     setEvaluatorType(type);
@@ -256,6 +264,15 @@ export function useAddEvaluatorWizard() {
     [nextStep]
   );
 
+  const setKmsKeyArn = useCallback(
+    (arn: string) => {
+      setKmsKeyArnState(arn);
+      const next = nextStep('kms-key-arn');
+      if (next) setStep(next);
+    },
+    [nextStep]
+  );
+
   const reset = useCallback(() => {
     setEvaluatorType('code-based');
     setCodeBasedType('managed');
@@ -264,6 +281,7 @@ export function useAddEvaluatorWizard() {
     setLlmConfig(getDefaultLlmConfig().llmAsAJudge!);
     setLambdaArnState('');
     setTimeoutState(DEFAULT_CODE_TIMEOUT);
+    setKmsKeyArnState('');
     setStep('evaluator-type');
   }, []);
 
@@ -288,6 +306,7 @@ export function useAddEvaluatorWizard() {
     setCustomRatingScale,
     setLambdaArn,
     setTimeout,
+    setKmsKeyArn,
     reset,
   };
 }
diff --git a/src/lib/index.ts b/src/lib/index.ts
index d21baec86..5be75106d 100644
--- a/src/lib/index.ts
+++ b/src/lib/index.ts
@@ -28,3 +28,5 @@ export * from './utils';
 // Schema I/O utilities
 export * from './schemas/io';
 export * from './time-constants';
+export { serializeResult } from './result';
+export type { Result } from './result';
diff --git a/src/lib/result.ts b/src/lib/result.ts
new file mode 100644
index 000000000..abec578c3
--- /dev/null
+++ b/src/lib/result.ts
@@ -0,0 +1,30 @@
+/**
+ * Discriminated union for fallible operations, inspired by Rust's Result<T, E>.
+ *
+ * Success branch spreads T onto the result; failure branch carries an Error.
+ * E extends Error so callers always get stack traces, cause chains, and instanceof narrowing.
+ *
+ * @example
+ *   Result                                    // { success: true } | { success: false; error: Error }
+ *   Result<{ name: string }>                  // { success: true; name: string } | { success: false; error: Error }
+ *   Result<{ name: string }, ValidationError> // { success: true; name: string } | { success: false; error: ValidationError }
+ */
+// eslint-disable-next-line @typescript-eslint/no-empty-object-type
+export type Result<T extends Record<string, unknown> = {}, E extends Error = Error> =
+  | ({ success: true } & T)
+  | { success: false; error: E };
+
+/**
+ * Converts a Result object to a JSON-serializable form.
+ * Error objects have non-enumerable properties, so JSON.stringify produces `{}`.
+ * This replaces the `error` field with the error message string.
+ */
+export function serializeResult<T extends Record<string, unknown>>(
+  result: ({ success: true } & T) | ({ success: false; error: Error } & Record<string, unknown>)
+): Record<string, unknown> {
+  if (!result.success) {
+    const { error, ...rest } = result;
+    return { ...rest, error: error.message };
+  }
+  return result;
+}
diff --git a/src/schema/schemas/agentcore-project.ts b/src/schema/schemas/agentcore-project.ts
index 9ca28dfda..c5480bec7 100644
--- a/src/schema/schemas/agentcore-project.ts
+++ b/src/schema/schemas/agentcore-project.ts
@@ -11,7 +11,12 @@ import { AgentEnvSpecSchema } from './agent-env';
 import { AgentCoreGatewaySchema, AgentCoreGatewayTargetSchema, AgentCoreMcpRuntimeToolSchema } from './mcp';
 import { ABTestSchema } from './primitives/ab-test';
 import { ConfigBundleSchema } from './primitives/config-bundle';
-import { EvaluationLevelSchema, EvaluatorConfigSchema, EvaluatorNameSchema } from './primitives/evaluator';
+import {
+  EvaluationLevelSchema,
+  EvaluatorConfigSchema,
+  EvaluatorNameSchema,
+  KmsKeyArnSchema,
+} from './primitives/evaluator';
 import { HarnessNameSchema } from './primitives/harness';
 import { HttpGatewaySchema } from './primitives/http-gateway';
 import {
@@ -46,7 +51,13 @@ export type {
   ManagedCodeBasedConfig,
   RatingScale,
 } from './primitives/evaluator';
-export { BedrockModelIdSchema, isValidBedrockModelId, EvaluatorNameSchema } from './primitives/evaluator';
+export {
+  BedrockModelIdSchema,
+  isValidBedrockModelId,
+  EvaluatorNameSchema,
+  KMS_KEY_ARN_PATTERN,
+  isValidKmsKeyArn,
+} from './primitives/evaluator';
 export { ConfigBundleSchema };
 export type { ComponentConfiguration, ComponentConfigurationMap, ConfigBundle } from './primitives/config-bundle';
 export { ConfigBundleNameSchema, ComponentConfigurationMapSchema } from './primitives/config-bundle';
@@ -220,6 +231,7 @@ export const EvaluatorSchema = z.object({
   level: EvaluationLevelSchema,
   description: z.string().optional(),
   config: EvaluatorConfigSchema,
+  kmsKeyArn: KmsKeyArnSchema.optional(),
   tags: TagsSchema.optional(),
 });
 
diff --git a/src/schema/schemas/primitives/evaluator.ts b/src/schema/schemas/primitives/evaluator.ts
index aa4f41cb4..97d772d52 100644
--- a/src/schema/schemas/primitives/evaluator.ts
+++ b/src/schema/schemas/primitives/evaluator.ts
@@ -119,3 +119,25 @@ export const EvaluatorConfigSchema = z
   });
 
 export type EvaluatorConfig = z.infer<typeof EvaluatorConfigSchema>;
+
+// ============================================================================
+// KMS Key ARN Validation
+// ============================================================================
+
+/**
+ * Pattern for KMS key ARNs accepted by the AgentCore Evaluation service.
+ * Matches key ARNs across all AWS partitions with a 36-char UUID key ID.
+ * Alias ARNs are not supported by the service for evaluator encryption.
+ */
+export const KMS_KEY_ARN_PATTERN = /^arn:[^:]+:kms:[a-zA-Z0-9-]*:[0-9]{12}:key\/[a-zA-Z0-9-]{36}$/;
+
+export const KmsKeyArnSchema = z
+  .string()
+  .regex(
+    KMS_KEY_ARN_PATTERN,
+    'Must be a valid KMS key ARN (e.g. arn:aws:kms:us-east-1:123456789012:key/12345678-1234-1234-1234-123456789012)'
+  );
+
+export function isValidKmsKeyArn(value: string): boolean {
+  return KMS_KEY_ARN_PATTERN.test(value);
+}