diff --git a/tests/pester-tests/features/CygwinSource.Tests.ps1 b/tests/pester-tests/features/CygwinSource.Tests.ps1
new file mode 100644
index 0000000000..90f3b78ef6
--- /dev/null
+++ b/tests/pester-tests/features/CygwinSource.Tests.ps1
@@ -0,0 +1,30 @@
+Import-Module helpers/common-helpers
+
+# This is skipped when not run in CI because it modifies the local system.
+Describe "Cygwin Source" -Tag Chocolatey, CygwinSource -Skip:(-not $env:TEST_KITCHEN) {
+    BeforeAll {
+        Initialize-ChocolateyTestInstall
+        New-ChocolateyInstallSnapshot
+        Enable-ChocolateySource -Name hermes-setup
+        $null = Invoke-Choco install cygwin
+    }
+
+    AfterAll {
+        $null = Invoke-Choco uninstall cygwin --remove-dependencies
+        Remove-ChocolateyTestInstall
+    }
+
+    Context "install all" {
+        BeforeAll {
+            $Output = Invoke-Choco install all --source=cygwin
+        }
+
+        It 'Exits with exit code (1)' {
+            $Output.ExitCode | Should -Be 1 -Because $Output.String
+        }
+
+        It 'Outputs exception' {
+            $Output.Lines | Should -Contain "Alternative sources do not allow the use of the 'all' package name/keyword." -Because $Output.String
+        }
+    }
+}
\ No newline at end of file
diff --git a/tests/pester-tests/features/PythonSource.Tests.ps1 b/tests/pester-tests/features/PythonSource.Tests.ps1
index 63d91cf424..2a0aad6b67 100644
--- a/tests/pester-tests/features/PythonSource.Tests.ps1
+++ b/tests/pester-tests/features/PythonSource.Tests.ps1
@@ -27,12 +27,29 @@ Describe "Python Source" -Tag Chocolatey, UpgradeCommand, PythonSource, ProxySki
         }
 
         It 'Exits with correct exit code (<ExitCode>)' {
-            $Output.ExitCode | Should -Be $ExitCode
+            $Output.ExitCode | Should -Be $ExitCode -Because $Output.String
         }
 
         It 'Outputs properly' {
-            $Output.Lines | Should -Not:($ExitCode -eq 0) -Contain "Alternative sources do not allow the use of the 'all' package name/keyword."
-            $Output.Lines | Should  -Contain "Chocolatey upgraded $Count/$Count packages."
+            $Output.Lines | Should -Not:($ExitCode -eq 0) -Contain "Alternative sources do not allow the use of the 'all' package name/keyword." -Because $Output.String
+            $Output.Lines | Should  -Contain "Chocolatey upgraded $Count/$Count packages." -Because $Output.String
+        }
+    }
+
+    Context "install all" {
+        BeforeAll {
+            # For some reason under kitchen-pester we don't have pip on the path. This might be due to our snapshotting...
+            Import-Module $env:ChocolateyInstall/helpers/ChocolateyProfile.psm1
+            Update-SessionEnvironment
+            $Output = Invoke-Choco install all --source=python
+        }
+
+        It 'Exits with exit code (1)' {
+            $Output.ExitCode | Should -Be 1 -Because $Output.String
+        }
+
+        It 'Outputs exception' {
+            $Output.Lines | Should -Contain "Alternative sources do not allow the use of the 'all' package name/keyword." -Because $Output.String
         }
     }
 }
diff --git a/tests/pester-tests/features/RubySource.Tests.ps1 b/tests/pester-tests/features/RubySource.Tests.ps1
new file mode 100644
index 0000000000..83aba65f82
--- /dev/null
+++ b/tests/pester-tests/features/RubySource.Tests.ps1
@@ -0,0 +1,30 @@
+Import-Module helpers/common-helpers
+
+# This is skipped when not run in CI because it modifies the local system.
+Describe "Ruby Source" -Tag Chocolatey, RubySource -Skip:(-not $env:TEST_KITCHEN) {
+    BeforeAll {
+        Initialize-ChocolateyTestInstall
+        New-ChocolateyInstallSnapshot
+        Enable-ChocolateySource -Name hermes-setup
+        $null = Invoke-Choco install ruby.portable
+    }
+
+    AfterAll {
+        $null = Invoke-Choco uninstall ruby.portable --remove-dependencies
+        Remove-ChocolateyTestInstall
+    }
+
+    Context "install all" {
+        BeforeAll {
+            $Output = Invoke-Choco install all --source=ruby
+        }
+
+        It 'Exits with exit code (1)' {
+            $Output.ExitCode | Should -Be 1 -Because $Output.String
+        }
+
+        It 'Outputs exception' {
+            $Output.Lines | Should -Contain "Alternative sources do not allow the use of the 'all' package name/keyword." -Because $Output.String
+        }
+    }
+}
\ No newline at end of file
diff --git a/tests/pester-tests/features/WindowsFeaturesSource.Tests.ps1 b/tests/pester-tests/features/WindowsFeaturesSource.Tests.ps1
new file mode 100644
index 0000000000..53bd633ea0
--- /dev/null
+++ b/tests/pester-tests/features/WindowsFeaturesSource.Tests.ps1
@@ -0,0 +1,26 @@
+Import-Module helpers/common-helpers
+
+Describe "Windows Features Source" -Tag Chocolatey, WindowsFeaturesSource {
+    BeforeAll {
+        Initialize-ChocolateyTestInstall
+        New-ChocolateyInstallSnapshot
+    }
+
+    AfterAll {
+        Remove-ChocolateyTestInstall
+    }
+
+    Context "install all" {
+        BeforeAll {
+            $Output = Invoke-Choco install all --source=windowsfeatures
+        }
+
+        It 'Exits with exit code (1)' {
+            $Output.ExitCode | Should -Be 1 -Because $Output.String
+        }
+
+        It 'Outputs exception' {
+            $Output.Lines | Should -Contain "Alternative sources do not allow the use of the 'all' package name/keyword." -Because $Output.String
+        }
+    }
+}
\ No newline at end of file