diff --git a/.ado/windows-vs-pr.yml b/.ado/windows-vs-pr.yml
index 3a9f922b1bd..5bdccb68324 100644
--- a/.ado/windows-vs-pr.yml
+++ b/.ado/windows-vs-pr.yml
@@ -65,6 +65,13 @@ jobs:
         clean: false
         submodules: false
 
+      - task: PowerShell@2
+        displayName: "Check if this environment meets the development dependencies"
+        inputs:
+          targetType: filePath
+          filePath: $(Build.SourcesDirectory)\vnext\Scripts\rnw-dependencies.ps1
+          arguments: -NoPrompt
+
       - template: templates/build-rnw.yml
         parameters:
           yarnBuildCmd: build
diff --git a/change/react-native-windows-2020-05-11-17-22-16-rnw-dependencies.json b/change/react-native-windows-2020-05-11-17-22-16-rnw-dependencies.json
new file mode 100644
index 00000000000..c4d7af43b9f
--- /dev/null
+++ b/change/react-native-windows-2020-05-11-17-22-16-rnw-dependencies.json
@@ -0,0 +1,8 @@
+{
+  "type": "prerelease",
+  "comment": "add rnw-dependencies.ps1",
+  "packageName": "react-native-windows",
+  "email": "asklar@microsoft.com",
+  "dependentChangeType": "patch",
+  "date": "2020-05-12T00:22:16.000Z"
+}
diff --git a/docs/building-rnw.md b/docs/building-rnw.md
index 3dd61b188ae..7b09e5cbbbf 100644
--- a/docs/building-rnw.md
+++ b/docs/building-rnw.md
@@ -22,7 +22,7 @@ Note that react-native-windows is a monorepo and relies on monorepo tools like y
   There are two ways to run the app.  In a fully managed easy way, or by manually running all the required steps:
 
 ## Automatic
-The playground app can be run in a completely automatic way by using `react-native run-windows`.
+The playground app can be run in a completely automatic way by using `react-native run-windows --sln windows\playground.sln`.
 
 If you haven't already, install the react-native-cli  (One time only!)
 ```cmd
@@ -33,7 +33,7 @@ Then
 
 ```cmd
 cd packages\playground
-react-native run-windows
+react-native run-windows --sln windows\playground.sln
 ```
 
 ## Manual
diff --git a/vnext/Scripts/rnw-dependencies.ps1 b/vnext/Scripts/rnw-dependencies.ps1
new file mode 100644
index 00000000000..ab27b0519ff
--- /dev/null
+++ b/vnext/Scripts/rnw-dependencies.ps1
@@ -0,0 +1,147 @@
+# Troubleshoot RNW dependencies
+param([switch]$Install = $false, [switch]$NoPrompt = $false)
+$vsWorkloads = @( 'Microsoft.Component.MSBuild', 'Microsoft.VisualStudio.Component.VC.Tools.x86.x64', 'Microsoft.VisualStudio.ComponentGroup.UWP.Support');
+
+$v = [System.Environment]::OSVersion.Version;
+if ($env:Agent_BuildDirectory) {
+    $drive = (Resolve-Path $env:Agent_BuildDirectory).Drive
+} else {
+    $drive = (Resolve-Path $PSCommandPath).Drive
+}
+
+function CheckVS {
+    $vsWhere = "${env:ProgramFiles(x86)}\Microsoft Visual Studio\Installer\vswhere.exe"
+    if (!(Test-Path $vsWhere)) {
+        return $false;
+    }
+    $output = & $vsWhere -version 16 -requires $vsWorkloads -property productPath
+    return Test-Path $output;
+}
+
+function InstallVS {
+    $installerPath = "${env:ProgramFiles(x86)}\Microsoft Visual Studio\Installer";
+    $vsWhere = "$installerPath\vswhere.exe"
+    if (!(Test-Path $vsWhere)) {
+        # No VSWhere / VS_Installer
+        & choco install -y visualstudio2019community
+    }
+    $channelId = & $vsWhere -version 16 -property channelId
+    $productId = & $vsWhere -version 16 -property productId
+    $vsInstaller = "$installerPath\vs_installer.exe"
+    $addWorkloads = $vsWorkloads | % { '--add', $_ };
+    Start-Process -PassThru -Wait  -Path $vsInstaller -ArgumentList ("install --channelId $channelId --productId $productId $addWorkloads --quiet" -split ' ')
+
+}
+
+function CheckNode {
+    try {
+        $v = (Get-Command node).Version.Major
+        return $v -eq 12 -or $v -eq 13
+    } catch {
+        return $false;
+    }
+}
+
+function GetChocoPkgVersion{
+    params([string]$packageId)
+    [version]$version = (& choco list --local-only $packageId -r -e).Substring($packageId.Length + 1);
+    return $version;
+}
+
+$requiredFreeSpaceGB = 15;
+
+$requirements = @(
+    @{
+        Name = "Free space on $drive`: > $requiredFreeSpaceGB GB";
+        Valid = $drive.Free/1GB -gt $requiredFreeSpaceGB;
+        Optional = $true # this requirement is fuzzy 
+    },
+    @{
+        Name = 'Windows version > 10.0.16299.0';
+        Valid = ($v.Major -eq 10 -and $v.Minor -eq 0 -and $v.Build -ge 16299)
+    },
+    @{
+        Name = 'Developer mode is on';
+        Valid = try { (Get-WindowsDeveloperLicense).IsValid } catch { $false }
+    },
+    @{
+        Name = 'git';
+        Valid = try { (Get-Command git.exe) -ne $null } catch { $false }
+    }
+    @{
+        Name = 'Choco';
+        Valid = try { (Get-Command choco) -ne $null } catch { $false };
+        Install = {
+            [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; 
+            iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))
+        };
+    },
+    @{
+        Name = 'VS 2019 with UWP and Desktop/C++';
+        Valid = CheckVS
+    },
+    @{
+        Name = 'NodeJS 12 or 13 installed';
+        Valid = CheckNode
+        Install = { choco install -y nodejs.install --version=12.9.1 }
+    },
+    @{
+        Name = 'Chrome';
+        Valid = try { ((Get-Item (Get-ItemProperty 'HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\App Paths\chrome.exe').'(Default)').VersionInfo).ProductMajorPart
+        } catch { $false } ;
+        Install = { choco install -y GoogleChrome }
+    },
+    @{
+        Name = 'Yarn';
+        Valid = try { (Get-Command yarn) -ne $null } catch { $false };
+        Install = { choco install -y yarn }
+    },
+    @{
+        Name = 'Appium';
+        Valid = (Test-Path "${env:ProgramFiles}\Appium\Appium.exe");
+        Install = { choco install -y Appium-desktop };
+        Optional = $true
+    },
+    @{
+        Name = 'WinAppDriver';
+        Valid = (Test-Path "${env:ProgramFiles(x86)}\Windows Application Driver\WinAppDriver.exe");
+        Install = { choco install -y WinAppDriver };
+    }
+
+    );
+
+function IsElevated {
+    return [bool](([System.Security.Principal.WindowsIdentity]::GetCurrent()).groups -match "S-1-5-32-544");
+}
+
+if (!(IsElevated)) {
+    Write-Output "rnw-dependencies - this script must run elevated. Exiting.";
+    return;
+}
+
+$NeedsRerun = $false
+foreach ($req in $requirements)
+{
+    Write-Output "Checking $($req.Name)";
+    if (!($req.Valid)) {
+        Write-Output "Requirement failed: $($req.Name)";
+        if ($req.Install) {
+            if ($Install -or (!$NoPrompt -and (Read-Host "Do you want to install? ").ToUpperInvariant() -eq 'Y')) {
+                Invoke-Command $req.Install -ErrorAction Stop
+                if ($LASTEXITCODE -ne 0) { throw "Last exit code was non-zero: $LASTEXITCODE"; }
+            } elseif (!$req.Optional) {
+                $NeedsRerun = $true;
+            }
+        } else {
+            $NeedsRerun = !($req.Optional);
+        }
+    }
+}
+
+if ($NeedsRerun) {
+    Write-Output "Some dependencies are not met. Re-run with -Install to install them.";
+    exit 1;
+} else {
+    Write-Output "All mandatory requirements met";
+    exit 0;
+}