diff --git a/.github/workflows/test-deprecated-tags.yml b/.github/workflows/test-deprecated-tags.yml
new file mode 100644
index 0000000..965d260
--- /dev/null
+++ b/.github/workflows/test-deprecated-tags.yml
@@ -0,0 +1,59 @@
+name: Test versions.json
+on:
+  workflow_dispatch:
+  pull_request:
+    paths:
+    - versions.json
+    - versions.schema.json
+    - .github/workflows/test-deprecated-tags.yml
+
+jobs:
+  validate_json:
+    name: Validate json against schema
+    
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v4
+        with:
+          fetch-depth: 0
+      - uses: actions/setup-python@v5
+        with:
+          python-version: '3.13'
+      - run: pip install json-spec
+      - run: json validate --schema-file=versions.schema.json --document-file=versions.json
+
+  get_deprecated_tags:
+    name: Get deprecated version latest tags
+    runs-on: ubuntu-latest
+    needs: validate_json
+    outputs:
+      deprecatedVersionLatestTags: ${{ steps.tags.outputs.latestTags }}
+      
+    steps:
+      - uses: actions/checkout@v4
+        with:
+          fetch-depth: 0
+
+      - name: parse versions.json
+        id: tags
+        run: |
+          deprecatedLatestTags=$(jq -c "[.deprecations | to_entries | .[].value.latestTag]" versions.json)
+          echo "latestTags=$deprecatedLatestTags" >> $GITHUB_OUTPUT
+          echo "latestTags=$deprecatedLatestTags"
+
+  test_docker_pull:
+    name: Test via docker pull
+    runs-on: ubuntu-latest
+    needs: get_deprecated_tags
+    strategy:
+      matrix: 
+        latestTag: ${{ fromJSON(needs.get_deprecated_tags.outputs.deprecatedVersionLatestTags) }}
+
+    steps:
+      - name: Log Inputs
+        run: |
+          echo "Deprecated Version Latest Tag: ${{ matrix.latestTag }}"
+
+      - name: Attempt Docker Pull
+        run: |
+          docker pull octopusdeploy/kubernetes-agent-tools-base:${{matrix.latestTag}}
diff --git a/versions.schema.json b/versions.schema.json
new file mode 100644
index 0000000..9ef5c8c
--- /dev/null
+++ b/versions.schema.json
@@ -0,0 +1,68 @@
+{  
+  "$schema": "http://json-schema.org/draft-04/schema#",
+  "description": "kubernetes-agent-tools-base versions",
+  "type": "object",
+  "properties": {
+    "tools": {
+      "type": "object",
+      "properties": {
+        "kubectl": {
+          "type": "array",
+          "items": {
+            "type": "string"
+          }
+        },
+        "helm": {
+          "type": "array",
+          "items": {
+            "type": "string"
+          }
+        },
+        "powershell": {
+          "type": "array",
+          "items": {
+            "type": "string"
+          }
+        }
+      },
+      "required": [
+        "kubectl",
+        "helm",
+        "powershell"
+      ]
+    },
+    "latest": {
+      "type": "string",
+      "minLength": 1,
+      "maxLength": 4
+    },
+    "revisionHash": {
+      "type": "string",
+      "minLength": 1,
+      "maxLength": 6
+    },
+    "deprecations": {
+      "type": "object",
+      "pattenProperties": {
+        ".*": {
+          "type": "object",
+          "properties": {
+            "latestTag": {
+              "type": "string",
+              "minLength": 1
+            }
+          },
+          "required": [
+            "latestTag"
+          ]
+        }
+      }
+    }
+  },
+  "required": [
+    "tools",
+    "latest",
+    "revisionHash",
+    "deprecations"
+  ]
+}