diff --git a/images/macos/provision/core/apache.sh b/images/macos/provision/core/apache.sh
new file mode 100644
index 000000000..08639cba3
--- /dev/null
+++ b/images/macos/provision/core/apache.sh
@@ -0,0 +1,6 @@
+#!/bin/bash -e -o pipefail
+
+brew install httpd
+sudo sed -Ei '' 's/Listen .*/Listen 80/' $(brew --prefix)/etc/httpd/httpd.conf
+
+invoke_tests "WebServers" "Apache"
diff --git a/images/macos/provision/core/nginx.sh b/images/macos/provision/core/nginx.sh
new file mode 100644
index 000000000..616c19eed
--- /dev/null
+++ b/images/macos/provision/core/nginx.sh
@@ -0,0 +1,6 @@
+#!/bin/bash -e -o pipefail
+
+brew install nginx
+sudo sed -Ei '' 's/listen.*/listen 80;/' $(brew --prefix)/etc/nginx/nginx.conf
+
+invoke_tests "WebServers" "Nginx"
diff --git a/images/macos/software-report/SoftwareReport.Generator.ps1 b/images/macos/software-report/SoftwareReport.Generator.ps1
index 6cbb986e4..e3b50aeb4 100644
--- a/images/macos/software-report/SoftwareReport.Generator.ps1
+++ b/images/macos/software-report/SoftwareReport.Generator.ps1
@@ -14,6 +14,7 @@ Import-Module "$PSScriptRoot/SoftwareReport.Java.psm1" -DisableNameChecking
 Import-Module "$PSScriptRoot/SoftwareReport.Xamarin.psm1" -DisableNameChecking
 Import-Module "$PSScriptRoot/SoftwareReport.Toolcache.psm1" -DisableNameChecking
 Import-Module "$PSScriptRoot/SoftwareReport.Browsers.psm1" -DisableNameChecking
+Import-Module "$PSScriptRoot/SoftwareReport.WebServers.psm1" -DisableNameChecking
 Import-Module "$PSScriptRoot/../helpers/SoftwareReport.Helpers.psm1"
 Import-Module "$PSScriptRoot/../helpers/Common.Helpers.psm1"
 Import-Module "$PSScriptRoot/../helpers/Xcode.Helpers.psm1"
@@ -219,6 +220,11 @@ $markdown += New-MDHeader "PowerShell Modules" -Level 4
 $markdown += Get-PowerShellModules | New-MDTable
 $markdown += New-MDNewLine
 
+# Web Servers
+if ($os.IsHigherThanMojave) {
+    $markdown += Build-WebServersSection
+}
+
 # Xamarin section
 $markdown += New-MDHeader "Xamarin" -Level 3
 $markdown += New-MDHeader "Visual Studio for Mac" -Level 4
diff --git a/images/macos/software-report/SoftwareReport.WebServers.psm1 b/images/macos/software-report/SoftwareReport.WebServers.psm1
new file mode 100644
index 000000000..041325538
--- /dev/null
+++ b/images/macos/software-report/SoftwareReport.WebServers.psm1
@@ -0,0 +1,41 @@
+function Get-ApacheVersion {
+    $name = "httpd"
+    $port = 80
+    $version = brew list $name --versions | Take-Part -Part 1
+    $serviceStatus = (brew services list) -match $name | Take-Part -Part 1
+    $configFile = "$(brew --prefix)/etc/httpd/httpd.conf"
+    return [PsCustomObject]@{
+        "Name" = $name
+        "Version" = $version
+        "ConfigFile" = $configFile
+        "ServiceStatus" = $serviceStatus
+        "ListenPort" = $port
+    }
+}
+
+function Get-NginxVersion {
+    $name = "nginx"
+    $port = 80
+    $version = brew list $name --versions | Take-Part -Part 1
+    $serviceStatus = (brew services list) -match $name | Take-Part -Part 1
+    $configFile = "$(brew --prefix)/etc/nginx/nginx.conf"
+    return [PsCustomObject]@{
+        "Name" = $name
+        "Version" = $version
+        "ConfigFile" = $configFile
+        "ServiceStatus" = $serviceStatus
+        "ListenPort" = $port
+    }
+}
+
+function Build-WebServersSection {
+    $output = ""
+    $output += New-MDHeader "Web Servers" -Level 3
+    $output += @(
+        (Get-ApacheVersion),
+        (Get-NginxVersion)
+    ) | Sort-Object Name | New-MDTable
+
+    $output += New-MDNewLine
+    return $output
+}
diff --git a/images/macos/templates/macOS-10.15.json b/images/macos/templates/macOS-10.15.json
index 575f109f4..92b2f36c6 100644
--- a/images/macos/templates/macOS-10.15.json
+++ b/images/macos/templates/macOS-10.15.json
@@ -174,6 +174,8 @@
                 "./provision/core/xamarin-android-ndk.sh",
                 "./provision/core/vsmac.sh",
                 "./provision/core/nvm.sh",
+                "./provision/core/apache.sh",
+                "./provision/core/nginx.sh",
                 "./provision/core/postgresql.sh",
                 "./provision/core/mongodb.sh",
                 "./provision/core/audiodevice.sh",
diff --git a/images/macos/templates/macOS-11.0.json b/images/macos/templates/macOS-11.0.json
index 943e53d16..fb96ec821 100644
--- a/images/macos/templates/macOS-11.0.json
+++ b/images/macos/templates/macOS-11.0.json
@@ -173,6 +173,8 @@
                 "./provision/core/xamarin.sh",
                 "./provision/core/vsmac.sh",
                 "./provision/core/nvm.sh",
+                "./provision/core/apache.sh",
+                "./provision/core/nginx.sh",
                 "./provision/core/postgresql.sh",
                 "./provision/core/mongodb.sh",
                 "./provision/core/vcpkg.sh",
diff --git a/images/macos/tests/WebServers.Tests.ps1 b/images/macos/tests/WebServers.Tests.ps1
new file mode 100644
index 000000000..5bd1f116d
--- /dev/null
+++ b/images/macos/tests/WebServers.Tests.ps1
@@ -0,0 +1,19 @@
+Describe "Apache" {
+    It "Apache CLI" {
+        "httpd -v" | Should -ReturnZeroExitCode
+    }
+
+    It "Apache Service" {
+        brew services list | Out-String | Should -Match "httpd\s+stopped"
+    }
+}
+
+Describe "Nginx" {
+    It "Nginx CLI" {
+        "nginx -v" | Should -ReturnZeroExitCode
+    }
+
+    It "Nginx Service" {
+        brew services list | Out-String | Should -Match "nginx\s+stopped"
+    }
+}