diff --git a/CHANGELOG.md b/CHANGELOG.md
index bdb933cfa0..d0499fbd55 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,6 +3,7 @@
 ### Features
 
 - **config:** Allow Scoop to check if apps versioned as 'nightly' are outdated ([#5166](https://github.com/ScoopInstaller/Scoop/issues/5166))
+- **checkup:** Add Windows Developer Mode check ([#5233](https://github.com/ScoopInstaller/Scoop/issues/5233))
 
 ### Bug Fixes
 
diff --git a/lib/diagnostic.ps1 b/lib/diagnostic.ps1
index 5caf8e7c7e..e4cc97e6a2 100644
--- a/lib/diagnostic.ps1
+++ b/lib/diagnostic.ps1
@@ -53,3 +53,17 @@ function check_long_paths {
 
     return $true
 }
+
+function Get-WindowsDeveloperModeStatus {
+    $DevModRegistryPath = "HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\AppModelUnlock"
+    if (!(Test-Path -Path $DevModRegistryPath) -or (Get-ItemProperty -Path `
+        $DevModRegistryPath -Name AllowDevelopmentWithoutDevLicense -ErrorAction `
+        SilentlyContinue).AllowDevelopmentWithoutDevLicense -ne 1) {
+        warn "Windows Developer Mode is not enabled. Operations relevant to symlinks may fail without proper rights."
+        Write-Host "  You may read more about the symlinks support here:"
+        Write-Host "  https://blogs.windows.com/windowsdeveloper/2016/12/02/symlinks-windows-10/"
+        return $false
+    }
+
+    return $true
+}
diff --git a/libexec/scoop-checkup.ps1 b/libexec/scoop-checkup.ps1
index 3c6c5f4f50..a775ec3964 100644
--- a/libexec/scoop-checkup.ps1
+++ b/libexec/scoop-checkup.ps1
@@ -17,6 +17,7 @@ if ($adminPrivileges) {
 
 $issues += !(check_main_bucket)
 $issues += !(check_long_paths)
+$issues += !(Get-WindowsDeveloperModeStatus)
 
 if (!(Test-HelperInstalled -Helper 7zip)) {
     error "'7-Zip' is not installed! It's required for unpacking most programs. Please Run 'scoop install 7zip' or 'scoop install 7zip-zstd'."