diff --git a/.github/workflows/check-pinned-versions.yml b/.github/workflows/check-pinned-versions.yml
new file mode 100644
index 000000000..bda072158
--- /dev/null
+++ b/.github/workflows/check-pinned-versions.yml
@@ -0,0 +1,22 @@
+name: Check Outdated Version Pinning
+
+on:
+  schedule:
+    - cron: '0 12 * * 1'  # Run at 12:00 UTC every Monday
+
+permissions:
+  issues: write
+  contents: read
+
+jobs:
+  check-pinning-dates:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v3
+
+      - name: Validate JSON Schema
+        shell: pwsh
+        run: ./helpers/CheckOutdatedVersionPinning.ps1
+        env:
+          GH_TOKEN: ${{ github.token }}
diff --git a/.github/workflows/validate-json-schema.yml b/.github/workflows/validate-json-schema.yml
new file mode 100644
index 000000000..dbebc0f29
--- /dev/null
+++ b/.github/workflows/validate-json-schema.yml
@@ -0,0 +1,20 @@
+name: Validate JSON Schema
+
+on:
+  push:
+    branches:
+      - main
+  pull_request:
+    branches:
+      - main
+
+jobs:
+  validate-json-schema:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v3
+
+      - name: Validate JSON Schema
+        shell: pwsh
+        run: ./helpers/CheckJsonSchema.ps1
diff --git a/.vscode/settings.json b/.vscode/settings.json
index f0ce6b6ac..98a58c65f 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -21,5 +21,14 @@
   ],
   "shellcheck.customArgs": [
     "-x"
-  ]
+  ],
+  "json.schemas": [
+    {
+        "fileMatch": [
+            "**/toolset-*.json"
+        ],
+        "url": "./schemas/toolset-schema.json"
+    }
+]
+
 }
diff --git a/helpers/CheckJsonSchema.ps1 b/helpers/CheckJsonSchema.ps1
new file mode 100644
index 000000000..4155fb899
--- /dev/null
+++ b/helpers/CheckJsonSchema.ps1
@@ -0,0 +1,42 @@
+$ErrorActionPreference = 'Stop'
+
+# A JSON schema validator which supports outputting line numbers for errors
+# this allows us to put annotations on builds for errors in the JSON files
+# `Test-Json` built in cmdline doesn't. No existing cli tool supports this
+# that I could find either. See: https://github.com/lawrencegripper/gripdev-json-schema-validator
+Install-Module -Name GripDevJsonSchemaValidator -Force -Scope CurrentUser
+
+# Find all toolset JSON files
+$toolsetFiles = Get-ChildItem -Recurse -Filter "toolset-*.json" | Where-Object { $_.Name -notlike "*schema.json" }
+$schemaFilePath = "./schemas/toolset-schema.json"
+
+$toolsetHasErrors = $false
+foreach ($file in $toolsetFiles) {
+    Write-Host ""
+    Write-Host "🔍 Validating $($file.FullName)" -ForegroundColor Cyan
+
+    $validationResult = Test-JsonSchema -SchemaPath $schemaFilePath -JsonPath $file.FullName -PrettyPrint $false
+
+    if ($validationResult.Valid) {
+        Write-Host "✅ JSON is valid." -ForegroundColor Green
+    } else {
+        # File has been modified since the commit, enforce validation
+        $toolsetHasErrors = $true
+        Write-Host "`n❌ JSON validation failed!" -ForegroundColor Red
+        Write-Host "   Found the following errors:`n" -ForegroundColor Yellow
+
+        $validationResult.Errors | ForEach-Object {
+            Write-Host $_.UserMessage
+            if ($env:GITHUB_ACTIONS -eq 'true') {
+                Write-Host "Adding annotation"
+                Write-Host "::error file=$($file.Name),line=$($_.LineNumber)::$($_.UserMessage.Replace("`n", '%0A'))"
+            }
+        }
+    }
+}
+
+if ($toolsetHasErrors) {
+    Write-Error "One or more toolset JSON files failed schema validation. See the error output above for more details."
+} else {
+    Write-Host "Schema validation completed successfully"
+}
diff --git a/helpers/CheckOutdatedVersionPinning.ps1 b/helpers/CheckOutdatedVersionPinning.ps1
new file mode 100644
index 000000000..2d98ad587
--- /dev/null
+++ b/helpers/CheckOutdatedVersionPinning.ps1
@@ -0,0 +1,85 @@
+$ErrorActionPreference = 'Stop'
+
+# Find all toolset JSON files
+$toolsetFiles = Get-ChildItem -Recurse -Filter "toolset-*.json" | Where-Object { $_.Name -notlike "*schema.json" }
+
+$expiringPins = @()
+$now = Get-Date
+$warningDays = 30 # Warn if expiring within 30 days
+
+foreach ($file in $toolsetFiles) {
+    Write-Host "Processing $($file.Name)"
+    $content = Get-Content $file.FullName | ConvertFrom-Json
+
+    # Recursively search for pinnedDetails in the JSON
+    function Search-PinnedDetails {
+        param($obj, $path)
+        
+        $foundPins = @()
+        
+        if ($obj -is [System.Management.Automation.PSCustomObject]) {
+            foreach ($prop in $obj.PSObject.Properties) {
+                if ($prop.Name -eq "pinnedDetails") {
+                    Write-Host "Found pinned version at $path"
+                    $reviewAt = [DateTime]::Parse($prop.Value.'review-at')
+                    $daysUntilExpiry = ($reviewAt - $now).Days
+                    
+                    if ($daysUntilExpiry -lt $warningDays) {
+                        Write-Host "Adding to expiringPins array"
+                        $foundPins += @{
+                            Path = $path
+                            File = $file.Name
+                            ReviewAt = $reviewAt
+                            DaysUntilExpiry = $daysUntilExpiry
+                            Reason = $prop.Value.reason
+                            Link = $prop.Value.link
+                        }
+                    }
+                } else {
+                    $foundPins += Search-PinnedDetails -obj $prop.Value -path "$path.$($prop.Name)"
+                }
+            }
+        } elseif ($obj -is [Array]) {
+            for ($i = 0; $i -lt $obj.Count; $i++) {
+                $foundPins += Search-PinnedDetails -obj $obj[$i] -path "$path[$i]"
+            }
+        }
+        
+        return $foundPins
+    }
+
+    $expiringPins += Search-PinnedDetails -obj $content -path $file.Name
+}
+
+if ($expiringPins) {
+    $issueBody = "# Version Pinning Review Required`n`n"
+    $issueBody += "The following pinned versions need review:`n`n"
+    
+    foreach ($pin in $expiringPins) {
+        $status = if ($pin.DaysUntilExpiry -lt 0) { "EXPIRED" } else { "Expiring Soon" }
+        $issueBody += "## $($status) - $($pin.Path)`n"
+        $issueBody += "- **File**: $($pin.File)`n"
+        $issueBody += "- **Review Date**: $($pin.ReviewAt.ToString('yyyy-MM-dd'))`n"
+        $issueBody += "- **Days until expiry**: $($pin.DaysUntilExpiry)`n"
+        $issueBody += "- **Reason**: $($pin.Reason)`n"
+        $issueBody += "- **Original PR**: $($pin.Link)`n`n"
+    }
+
+    if ($env:GITHUB_ACTIONS -eq 'true') {
+        # In GitHub Actions, create an issue
+        Write-Host "Creating issue"
+        $tempFile = [System.IO.Path]::GetTempFileName()
+        Set-Content -Path $tempFile -Value $issueBody
+        gh issue create --title "Version Pinning Review Found Expired Pinned Versions" --body-file $tempFile
+        Remove-Item -Path $tempFile
+    }
+    
+    Write-Host "`nIssue Content:`n"
+    Write-Host $issueBody
+}
+else {
+    Write-Host "No expiring pins found."
+    if ($env:GITHUB_ACTIONS -eq 'true') {
+        "expired_pins=0" >> $env:GITHUB_OUTPUT
+    }
+}
diff --git a/images/ubuntu/toolsets/toolset-2004.json b/images/ubuntu/toolsets/toolset-2004.json
index 1f872bd89..047044b6b 100644
--- a/images/ubuntu/toolsets/toolset-2004.json
+++ b/images/ubuntu/toolsets/toolset-2004.json
@@ -381,10 +381,21 @@
     },
     "aliyunCli": {
         "version": "3.0.174",
-        "sha256": "0c51028a7a32fc02c8de855f73e273556f957115eb5624565738f9b9f83a50ba"
+        "sha256": "0c51028a7a32fc02c8de855f73e273556f957115eb5624565738f9b9f83a50ba",
+        "pinnedDetails": {
+            "link": "https://github.com/actions/runner-images-internal/pull/6702",
+            "reason": "Meaningful reason must be added at next update.",
+            "review-at": "2025-06-01",
+            "type": "preexisting-pinned-version-without-reason"
+        }
     },
     "ocCli": {
-        "version": "4.15.19"
-    } 
-      
+        "version": "4.15.19",
+        "pinnedDetails": {
+            "link": "https://github.com/actions/runner-images-internal/pull/6702",
+            "reason": "Meaningful reason must be added at next update.",
+            "review-at": "2025-06-01",
+            "type": "preexisting-pinned-version-without-reason"
+        }
+    }
 }
diff --git a/images/windows/toolsets/toolset-2019.json b/images/windows/toolsets/toolset-2019.json
index 4ff1a44fc..d547586c2 100644
--- a/images/windows/toolsets/toolset-2019.json
+++ b/images/windows/toolsets/toolset-2019.json
@@ -474,7 +474,12 @@
         "version": "latest"
     },
     "openssl": {
-        "version": "1.1.1"
+        "version": "1.1.1",
+        "pinnedDetails": {
+            "link": "https://github.com/somelink",
+            "reason": "this was pinned due to a downstream issue with the installer",
+            "review-at": "2025-01-30"
+        }
     },
     "pwsh": {
         "version": "7.4"
diff --git a/images/windows/toolsets/toolset-2022.json b/images/windows/toolsets/toolset-2022.json
index 4fbce97d2..6660ef26a 100644
--- a/images/windows/toolsets/toolset-2022.json
+++ b/images/windows/toolsets/toolset-2022.json
@@ -150,7 +150,13 @@
     },
     "mingw": {
         "version": "12.2.0",
-        "runtime": "ucrt"
+        "runtime": "ucrt",
+        "pinnedDetails": {
+            "link": "https://github.com/actions/runner-images-internal/pull/6702",
+            "reason": "Meaningful reason must be added at next update.",
+            "review-at": "2025-06-01",
+            "type": "preexisting-pinned-version-without-reason"
+        }
     },
     "MsysPackages": {
         "msys2": [],
@@ -384,7 +390,13 @@
         "version": "latest"
     },
     "openssl": {
-        "version": "1.1.1"
+        "version": "1.1.1",
+        "pinnedDetails": {
+            "link": "https://github.com/actions/runner-images-internal/pull/6702",
+            "reason": "Meaningful reason must be added at next update.",
+            "review-at": "2024-06-01",
+            "type": "preexisting-pinned-version-without-reason"
+        }
     },
     "pwsh": {
         "version": "7.4"
diff --git a/images/windows/toolsets/toolset-2025.json b/images/windows/toolsets/toolset-2025.json
index 6cf6ffc93..22e3b5ef5 100644
--- a/images/windows/toolsets/toolset-2025.json
+++ b/images/windows/toolsets/toolset-2025.json
@@ -107,7 +107,13 @@
     },
     "mingw": {
         "version": "14.2.0",
-        "runtime": "ucrt"
+        "runtime": "ucrt",
+        "pinnedDetails": {
+            "link": "https://github.com/actions/runner-images-internal/pull/6702",
+            "reason": "Meaningful reason must be added at next update.",
+            "review-at": "2025-06-01",
+            "type": "preexisting-pinned-version-without-reason"
+        }
     },
     "MsysPackages": {
         "msys2": [],
@@ -318,7 +324,13 @@
         "version": "latest"
     },
     "openssl": {
-        "version": "3.4.0"
+        "version": "3.4.0",
+        "pinnedDetails": {
+            "link": "https://github.com/actions/runner-images-internal/pull/6702",
+            "reason": "Meaningful reason must be added at next update.",
+            "review-at": "2025-06-01",
+            "type": "preexisting-pinned-version-without-reason"
+        }
     },
     "pwsh": {
         "version": "7.4"
diff --git a/schemas/toolset-schema.json b/schemas/toolset-schema.json
new file mode 100644
index 000000000..f9bf71b96
--- /dev/null
+++ b/schemas/toolset-schema.json
@@ -0,0 +1,42 @@
+{
+  "$schema": "http://json-schema.org/draft-07/schema#",
+  "type": "object",
+  "patternProperties": {
+    "^.*$": {
+      "if": {
+        "type": "object",
+        "required": [
+          "version"
+        ],
+        "properties": {
+          "version": {
+            "type": "string",
+            "pattern": "^[0-9]+\\.[0-9]+\\.[0-9]+.*$"
+          }
+        }
+      },
+      "then": {
+        "required": [
+          "pinnedDetails"
+        ],
+        "properties": {
+          "pinnedDetails": {
+            "type": "object",
+            "properties": {
+              "reason": {
+                "type": "string"
+              },
+              "link": {
+                "type": "string"
+              },
+              "review-at": {
+                "type": "string",
+                "format": "date"
+              }
+            }
+          }
+        }
+      }
+    }
+  }
+}