diff --git a/pipelines/build/common/openjdk_build_pipeline.groovy b/pipelines/build/common/openjdk_build_pipeline.groovy
index 275d2e627..d4cb58dce 100644
--- a/pipelines/build/common/openjdk_build_pipeline.groovy
+++ b/pipelines/build/common/openjdk_build_pipeline.groovy
@@ -1563,57 +1563,64 @@ class Build {
                                                     echo "Signing $f using Eclipse Foundation codesign service"
                                                     dir=$(dirname "$f")
                                                     file=$(basename "$f")
-                                                    mv "$f" "${dir}/unsigned_${file}"
-                                                    success=false
-                                                    if [ "${base_os}" == "mac" ]; then
-                                                        if ! curl --fail --silent --show-error -o "$f" -F file="@${dir}/unsigned_${file}" -F entitlements="@$ENTITLEMENTS" https://cbi.eclipse.org/macos/codesign/sign; then
-                                                            echo "curl command failed, sign of $f failed"
-                                                        else
-                                                            success=true
-                                                        fi
-                                                    else
+                                                    ms_file_skipped=false
+                                                    if [ "${base_os}" == "windows" ]; then
+                                                        # Check if file is a Microsoft supplied file that is already signed
                                                         if [[ "$file" =~ api-ms-win.* ]] || [[ "$file" =~ msvcp.* ]] || [[ "$file" =~ ucrtbase.* ]] || [[ "$file" =~ vcruntime.* ]]; then
                                                             echo "Skipping Microsoft file $file"
-                                                            success=true
-                                                        elif ! curl --fail --silent --show-error -o "$f" -F file="@${dir}/unsigned_${file}" https://cbi.eclipse.org/authenticode/sign; then
-                                                            echo "curl command failed, sign of $f failed"
-                                                        else
-                                                            success=true
+                                                            ms_file_skipped=true
                                                         fi
                                                     fi
-                                                    if [ $success == false ]; then
-                                                        # Retry up to 20 times
-                                                        max_iterations=20
-                                                        iteration=1
-                                                        echo "Code Not Signed For File $f"
-                                                        while [ $iteration -le $max_iterations ] && [ $success = false ]; do
-                                                            echo $iteration Of $max_iterations
-                                                            sleep 1
-                                                            if [ "${base_os}" == "mac" ]; then
-                                                                if curl --fail --silent --show-error -o "$f" -F file="@${dir}/unsigned_${file}" -F entitlements="@$ENTITLEMENTS" https://cbi.eclipse.org/macos/codesign/sign; then
-                                                                    success=true
-                                                                fi
+                                                    if [ $ms_file_skipped == false ]; then
+                                                        mv "$f" "${dir}/unsigned_${file}"
+                                                        success=false
+                                                        if [ "${base_os}" == "mac" ]; then
+                                                            if ! curl --fail --silent --show-error -o "$f" -F file="@${dir}/unsigned_${file}" -F entitlements="@$ENTITLEMENTS" https://cbi.eclipse.org/macos/codesign/sign; then
+                                                                echo "curl command failed, sign of $f failed"
                                                             else
-                                                                if curl --fail --silent --show-error -o "$f" -F file="@${dir}/unsigned_${file}" https://cbi.eclipse.org/authenticode/sign; then
-                                                                    success=true
-                                                                fi
+                                                                success=true
                                                             fi
-
-                                                            if [ $success = false ]; then
-                                                                echo "curl command failed, $f Failed Signing On Attempt $iteration"
-                                                                iteration=$((iteration+1))
-                                                                if [ $iteration -gt $max_iterations ]
-                                                                then
-                                                                    echo "Errors Encountered During Signing"
-                                                                    exit 1
-                                                                fi
+                                                        else
+                                                            if ! curl --fail --silent --show-error -o "$f" -F file="@${dir}/unsigned_${file}" https://cbi.eclipse.org/authenticode/sign; then
+                                                                echo "curl command failed, sign of $f failed"
                                                             else
-                                                                echo "$f Signed OK On Attempt $iteration"
+                                                                success=true
                                                             fi
-                                                        done
-                                                    fi
-                                                    chmod --reference="${dir}/unsigned_${file}" "$f"
-                                                    rm -rf "${dir}/unsigned_${file}"
+                                                        fi
+                                                        if [ $success == false ]; then
+                                                            # Retry up to 20 times
+                                                            max_iterations=20
+                                                            iteration=1
+                                                            echo "Code Not Signed For File $f"
+                                                            while [ $iteration -le $max_iterations ] && [ $success = false ]; do
+                                                                echo $iteration Of $max_iterations
+                                                                sleep 1
+                                                                if [ "${base_os}" == "mac" ]; then
+                                                                    if curl --fail --silent --show-error -o "$f" -F file="@${dir}/unsigned_${file}" -F entitlements="@$ENTITLEMENTS" https://cbi.eclipse.org/macos/codesign/sign; then
+                                                                        success=true
+                                                                    fi
+                                                                else
+                                                                    if curl --fail --silent --show-error -o "$f" -F file="@${dir}/unsigned_${file}" https://cbi.eclipse.org/authenticode/sign; then
+                                                                        success=true
+                                                                    fi
+                                                                fi
+
+                                                                if [ $success = false ]; then
+                                                                    echo "curl command failed, $f Failed Signing On Attempt $iteration"
+                                                                    iteration=$((iteration+1))
+                                                                    if [ $iteration -gt $max_iterations ]
+                                                                    then
+                                                                        echo "Errors Encountered During Signing"
+                                                                        exit 1
+                                                                    fi
+                                                                else
+                                                                    echo "$f Signed OK On Attempt $iteration"
+                                                                fi
+                                                            done
+                                                        fi
+                                                        chmod --reference="${dir}/unsigned_${file}" "$f"
+                                                        rm -rf "${dir}/unsigned_${file}"
+                                                    fi # ms_file_skipped == false
                                                 done
                                             '''
                                             // groovylint-enable