diff --git a/images/macos/scripts/build/install-ruby.sh b/images/macos/scripts/build/install-ruby.sh
index e93ca6ab2df1..413e89349eda 100644
--- a/images/macos/scripts/build/install-ruby.sh
+++ b/images/macos/scripts/build/install-ruby.sh
@@ -12,8 +12,10 @@ echo "Installing Ruby..."
 brew_smart_install "ruby@${DEFAULT_RUBY_VERSION}"
 if [[ $arch == "arm64" ]]; then
     export PATH=/opt/homebrew/opt/ruby@${DEFAULT_RUBY_VERSION}/bin:$PATH
+    ruby_suffix="macos-13-arm64"
 else
     export PATH=/usr/local/opt/ruby@${DEFAULT_RUBY_VERSION}/bin:$PATH
+    ruby_suffix="macos-latest"
 fi
 
 GEM_PATH=$(gem env|awk '/EXECUTABLE DIRECTORY/ {print $4}')
@@ -24,37 +26,36 @@ else
     echo 'export PATH="$GEM_PATH:/usr/local/opt/ruby@'${DEFAULT_RUBY_VERSION}'/bin:$PATH"'  >> $HOME/.bashrc
 fi
 
-if ! is_Arm64; then
-    echo "Install Ruby from toolset..."
-    [ -n "$API_PAT" ] && authString=(-H "Authorization: token ${API_PAT}")
-    PACKAGE_TAR_NAMES=$(curl "${authString[@]}" -fsSL "https://api.github.com/repos/ruby/ruby-builder/releases/latest" | jq -r '.assets[].name')
-    TOOLSET_VERSIONS=$(get_toolset_value '.toolcache[] | select(.name | contains("Ruby")) | .arch.'$arch'.versions[]')
-    RUBY_PATH=$AGENT_TOOLSDIRECTORY/Ruby
+echo "Install Ruby from toolset..."
+[ -n "$API_PAT" ] && authString=(-H "Authorization: token ${API_PAT}")
+PACKAGE_TAR_NAMES=$(curl "${authString[@]}" -fsSL "https://api.github.com/repos/ruby/ruby-builder/releases/latest" | jq -r '.assets[].name')
+TOOLSET_VERSIONS=$(get_toolset_value '.toolcache[] | select(.name | contains("Ruby")) | .arch.'$arch'.versions[]')
+RUBY_PATH=$AGENT_TOOLSDIRECTORY/Ruby
 
-    echo "Check if Ruby hostedtoolcache folder exists..."
-    if [[ ! -d $RUBY_PATH ]]; then
-        mkdir -p $RUBY_PATH
-    fi
-    echo "ruby path - $RUBY_PATH "
-    for TOOLSET_VERSION in ${TOOLSET_VERSIONS[@]}; do
-        PACKAGE_TAR_NAME=$(echo "$PACKAGE_TAR_NAMES" | grep "^ruby-${TOOLSET_VERSION}-macos-latest.tar.gz$" | egrep -v "rc|preview" | sort -V | tail -1)
-        RUBY_VERSION=$(echo "$PACKAGE_TAR_NAME" | cut -d'-' -f 2)
-        RUBY_VERSION_PATH="$RUBY_PATH/$RUBY_VERSION"
-
-        echo "Create Ruby $RUBY_VERSION directory..."
-        mkdir -p $RUBY_VERSION_PATH
-
-        echo "Downloading tar archive $PACKAGE_TAR_NAME"
-        ARCHIVE_PATH=$(download_with_retry "https://github.com/ruby/ruby-builder/releases/download/toolcache/${PACKAGE_TAR_NAME}")
-
-        echo "Expand $PACKAGE_TAR_NAME to the $RUBY_VERSION_PATH folder"
-        tar xf $ARCHIVE_PATH -C $RUBY_VERSION_PATH
-        COMPLETE_FILE_PATH=$RUBY_VERSION_PATH/x64.complete
-        if [[ ! -f $COMPLETE_FILE_PATH ]]; then
-            echo "Create complete file"
-            touch $COMPLETE_FILE_PATH
-        fi
-    done
+echo "Check if Ruby hostedtoolcache folder exists..."
+if [[ ! -d $RUBY_PATH ]]; then
+    mkdir -p $RUBY_PATH
 fi
+echo "ruby path - $RUBY_PATH"
+
+for toolset_version in ${TOOLSET_VERSIONS[@]}; do
+    package_tar_name=$(echo "$PACKAGE_TAR_NAMES" | grep "^ruby-${toolset_version}-${ruby_suffix}.tar.gz$" | egrep -v "rc|preview" | sort -V | tail -1)
+    ruby_version=$(echo "$package_tar_name" | cut -d'-' -f 2)
+    ruby_version_path="$RUBY_PATH/$ruby_version"
+
+    echo "Create Ruby $ruby_version directory..."
+    mkdir -p $ruby_version_path
+
+    echo "Downloading tar archive $package_tar_name"
+    archive_path=$(download_with_retry "https://github.com/ruby/ruby-builder/releases/download/toolcache/${package_tar_name}")
+
+    echo "Expand $package_tar_name to the $ruby_version_path folder"
+    tar xf $archive_path -C $ruby_version_path
+    complete_file_path=$ruby_version_path/$arch.complete
+    if [[ ! -f $complete_file_path ]]; then
+        echo "Create complete file"
+        touch $complete_file_path
+    fi
+done
 
-invoke_tests "Ruby.$arch"
+invoke_tests "Ruby"
diff --git a/images/macos/scripts/docs-gen/SoftwareReport.Toolcache.psm1 b/images/macos/scripts/docs-gen/SoftwareReport.Toolcache.psm1
index 40c028c83a91..67576ec0d552 100644
--- a/images/macos/scripts/docs-gen/SoftwareReport.Toolcache.psm1
+++ b/images/macos/scripts/docs-gen/SoftwareReport.Toolcache.psm1
@@ -42,13 +42,9 @@ function Build-ToolcacheSection {
             [ToolVersionsListNode]::new("PyPy", $(Get-ToolcachePyPyVersions), '^\d+\.\d+', "List")
         )
     }
-    if ((-not $os.IsVenturaArm64) -and (-not $os.IsSonomaArm64) -and (-not $os.IsSequoiaArm64)) {
-        $nodes += @(
-            [ToolVersionsListNode]::new("Ruby", $(Get-ToolcacheRubyVersions), '^\d+\.\d+', "List")
-        )
-    }
 
     $nodes += @(
+        [ToolVersionsListNode]::new("Ruby", $(Get-ToolcacheRubyVersions), '^\d+\.\d+', "List")
         [ToolVersionsListNode]::new("Python", $(Get-ToolcachePythonVersions), '^\d+\.\d+', "List"),
         [ToolVersionsListNode]::new("Node.js", $(Get-ToolcacheNodeVersions), '^\d+', "List"),
         [ToolVersionsListNode]::new("Go", $(Get-ToolcacheGoVersions), '^\d+\.\d+', "List")
diff --git a/images/macos/scripts/tests/Ruby.arm64.Tests.ps1 b/images/macos/scripts/tests/Ruby.Tests.ps1
similarity index 61%
rename from images/macos/scripts/tests/Ruby.arm64.Tests.ps1
rename to images/macos/scripts/tests/Ruby.Tests.ps1
index 45cc879f1a99..12dd0fc79361 100644
--- a/images/macos/scripts/tests/Ruby.arm64.Tests.ps1
+++ b/images/macos/scripts/tests/Ruby.Tests.ps1
@@ -1,9 +1,7 @@
 Import-Module "$PSScriptRoot/../helpers/Common.Helpers.psm1"
 Import-Module "$PSScriptRoot/Helpers.psm1" -DisableNameChecking
 
-$os = Get-OSVersion
-
-Describe "Ruby" -Skip:(-not $os.IsArm64) {
+Describe "Ruby" {
     It "Ruby is available" {
         "ruby --version" | Should -ReturnZeroExitCode
     }
@@ -13,10 +11,11 @@ Describe "Ruby" -Skip:(-not $os.IsArm64) {
     }
 
     It "Ruby tools are consistent" {
-        $expectedPrefix = "/opt/homebrew"
-        Get-ToolPath "ruby" | Should -Match "$($expectedPrefix)*"
-        Get-ToolPath "gem" | Should -Match "$($expectedPrefix)*"
-        Get-ToolPath "bundler" | Should -Match "$($expectedPrefix)*"
+        $os = Get-OSVersion
+        $expectedPrefix = if ($os.IsArm64) { "/opt/homebrew" } else { "/usr/local" }
+        Get-ToolPath "ruby"    | Should -Match "^$expectedPrefix.*"
+        Get-ToolPath "gem"     | Should -Match "^$expectedPrefix.*"
+        Get-ToolPath "bundler" | Should -Match "^$expectedPrefix.*"
     }
 
     It "Ruby gems permissions are valid" {
diff --git a/images/macos/scripts/tests/Ruby.x64.Tests.ps1 b/images/macos/scripts/tests/Ruby.x64.Tests.ps1
deleted file mode 100644
index b458278b3d25..000000000000
--- a/images/macos/scripts/tests/Ruby.x64.Tests.ps1
+++ /dev/null
@@ -1,26 +0,0 @@
-Import-Module "$PSScriptRoot/../helpers/Common.Helpers.psm1"
-Import-Module "$PSScriptRoot/Helpers.psm1" -DisableNameChecking
-
-$os = Get-OSVersion
-
-Describe "Ruby" -Skip:($os.IsArm64) {
-    It "Ruby is available" {
-        "ruby --version" | Should -ReturnZeroExitCode
-    }
-
-    It "Ruby is installed via HomeBrew" {
-        Get-ToolPath "ruby" | Should -Not -BeLike "/usr/bin/ruby*"
-    }
-
-    It "Ruby tools are consistent" {
-        $expectedPrefix = "/usr/local"
-        Get-ToolPath "ruby" | Should -Match "$($expectedPrefix)*"
-        Get-ToolPath "gem" | Should -Match "$($expectedPrefix)*"
-        Get-ToolPath "bundler" | Should -Match "$($expectedPrefix)*"
-    }
-
-    It "Ruby gems permissions are valid" {
-        "gem install bundle" | Should -ReturnZeroExitCode
-        "gem uninstall bundle" | Should -ReturnZeroExitCode
-    }
-}
diff --git a/images/macos/toolsets/toolset-13.json b/images/macos/toolsets/toolset-13.json
index 2c38a66330ab..0104dc07efe9 100644
--- a/images/macos/toolsets/toolset-13.json
+++ b/images/macos/toolsets/toolset-13.json
@@ -214,6 +214,14 @@
                         "3.2.*",
                         "3.3.*"
                     ]
+                },
+                "arm64": {
+                    "versions": [
+                        "3.0.*",
+                        "3.1.*",
+                        "3.2.*",
+                        "3.3.*"
+                    ]
                 }
             }
         }
diff --git a/images/macos/toolsets/toolset-14.json b/images/macos/toolsets/toolset-14.json
index daf2e755fcd5..6766c152c711 100644
--- a/images/macos/toolsets/toolset-14.json
+++ b/images/macos/toolsets/toolset-14.json
@@ -204,6 +204,14 @@
                         "3.2.*",
                         "3.3.*"
                     ]
+                },
+                "arm64": {
+                    "versions": [
+                        "3.0.*",
+                        "3.1.*",
+                        "3.2.*",
+                        "3.3.*"
+                    ]
                 }
             }
         }
diff --git a/images/macos/toolsets/toolset-15.json b/images/macos/toolsets/toolset-15.json
index 60f7d57a6a7b..feb17e6445b2 100644
--- a/images/macos/toolsets/toolset-15.json
+++ b/images/macos/toolsets/toolset-15.json
@@ -187,7 +187,15 @@
                 "x64": {
                     "versions": [
                         "3.1.*",
-                        "3.2.*"
+                        "3.2.*",
+                        "3.3.*"
+                    ]
+                },
+                "arm64": {
+                    "versions": [
+                        "3.1.*",
+                        "3.2.*",
+                        "3.3.*"
                     ]
                 }
             }