diff --git a/images/windows/scripts/build/Install-OpenSSL.ps1 b/images/windows/scripts/build/Install-OpenSSL.ps1
index 6b60acf8d..b830adb30 100644
--- a/images/windows/scripts/build/Install-OpenSSL.ps1
+++ b/images/windows/scripts/build/Install-OpenSSL.ps1
@@ -22,7 +22,7 @@ $installerHash = $null
 
 foreach ($key in $installerNames) {
     $installer = $installersAvailable.$key
-    if (($installer.light -eq $light) -and ($installer.arch -eq $arch) -and ($installer.bits -eq $bits) -and ($installer.installer -eq $installerType) -and ($installer.basever -eq $version)) {
+    if (($installer.light -eq $light) -and ($installer.arch -eq $arch) -and ($installer.bits -eq $bits) -and ($installer.installer -eq $installerType) -and ($installer.basever -like $version)) {
         $installerUrl = $installer.url
         $installerHash = $installer.sha512
     }
diff --git a/images/windows/toolsets/toolset-2019.json b/images/windows/toolsets/toolset-2019.json
index de0a2236d..77012fa30 100644
--- a/images/windows/toolsets/toolset-2019.json
+++ b/images/windows/toolsets/toolset-2019.json
@@ -445,9 +445,9 @@
     "openssl": {
         "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"
+            "link": "https://github.com/actions/runner-images/issues/12045",
+            "reason": "Image is deprecated and will be removed soon",
+            "review-at": "2027-01-01"
         }
     },
     "pwsh": {
diff --git a/images/windows/toolsets/toolset-2022.json b/images/windows/toolsets/toolset-2022.json
index 1c72fb00c..b80b91cf8 100644
--- a/images/windows/toolsets/toolset-2022.json
+++ b/images/windows/toolsets/toolset-2022.json
@@ -363,13 +363,7 @@
         "version": "latest"
     },
     "openssl": {
-        "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"
-        }
+        "version": "3.*"
     },
     "pwsh": {
         "version": "7.4"
diff --git a/images/windows/toolsets/toolset-2025.json b/images/windows/toolsets/toolset-2025.json
index 81efc427e..f3cd7e113 100644
--- a/images/windows/toolsets/toolset-2025.json
+++ b/images/windows/toolsets/toolset-2025.json
@@ -328,13 +328,7 @@
         "version": "latest"
     },
     "openssl": {
-        "version": "3.5.3",
-        "pinnedDetails": {
-            "link": "https://github.com/openssl/openssl/releases/tag/openssl-3.5.3",
-            "reason": "Installer not found for version 3.5.2",
-            "review-at": "2025-10-10",
-            "type": "preexisting-pinned-version-without-reason"
-        }
+        "version": "3.*"
     },
     "pwsh": {
         "version": "7.4"