diff --git a/tests/chocolatey-tests/choco-upgrade.Tests.ps1 b/tests/chocolatey-tests/choco-upgrade.Tests.ps1
new file mode 100644
index 0000000000..96809a3e09
--- /dev/null
+++ b/tests/chocolatey-tests/choco-upgrade.Tests.ps1
@@ -0,0 +1,155 @@
+Import-Module helpers/common-helpers
+
+Describe "choco upgrade" -Tag Chocolatey, UpgradeCommand {
+    BeforeAll {
+        Initialize-ChocolateyTestInstall
+
+        New-ChocolateyInstallSnapshot
+    }
+
+    AfterAll {
+        Remove-ChocolateyTestInstall
+    }
+
+    Context "Can upgrade packages with dependencies containing side by side installations and outdated dependency" {
+        BeforeAll {
+            Restore-ChocolateyInstallSnapshot
+
+            $null = Invoke-Choco install chocolatey-core.extension --version 1.3.0 --confirm
+            $null = Invoke-Choco install 7zip --version 16.04 --confirm
+            $null = Invoke-Choco install chocolatey-core.extension --version 1.3.5.1 --sxs --confirm
+
+            $Output = Invoke-Choco upgrade 7zip --version 21.7 --confirm
+        }
+
+        AfterAll {
+            $null = Invoke-Choco uninstall 7zip 7zip.install --confirm
+        }
+
+        It "Exits with Success (0)" {
+            $Output.ExitCode | Should -Be 0 -Because $Output.String
+        }
+
+        It "Upgrades version <OldVersion> of the package <Name>" -ForEach @(
+            @{ Name = "7zip"; OldVersion = "16.04" }
+            @{ Name = "7zip.install"; OldVersion = "16.04" }
+            @{ Name = "chocolatey-core.extension"; OldVersion = "1.3.0" }
+        ) {
+            "$env:ChocolateyInstall\lib\$Name\$Name.nuspec" | Should -Exist
+            [xml]$XML = Get-Content "$env:ChocolateyInstall\lib\$Name\$Name.nuspec"
+            $XML.package.metadata.version | Should -Not -Be $OldVersion
+        }
+
+        It "Have not upgraded side by side installation of <Name> v<Version>" -ForEach @(
+            @{ Name = "chocolatey-core.extension"; Version = "1.3.5.1" }
+        ) {
+            "$env:ChocolateyInstall\lib\$Name.$Version\$Name.$Version.nupkg" | Should -Exist
+            [xml]$XML = Get-Content "$env:ChocolateyInstall\lib\$Name.$Version\$Name.$Version.nuspec"
+            $XML.package.metadata.id | Should -Be $Name
+            $XML.package.metadata.version | Should -Be $Version
+        }
+
+        It "Outputs a message showing that upgrading was successful" {
+            $Output.String | SHould -Match "Chocolatey upgraded 3/3 packages\."
+        }
+    }
+
+    Context "Can upgrade packages with dependencies containing side by side installations and up to date dependency" {
+        BeforeAll {
+            Restore-ChocolateyInstallSnapshot
+
+            $null = Invoke-Choco install chocolatey-core.extension --version 1.3.3 --confirm
+            $null = Invoke-Choco install 7zip --version 16.04 --confirm
+            $null = Invoke-Choco install chocolatey-core.extension --version 1.3.5.1 --sxs --confirm
+
+            $Output = Invoke-Choco upgrade 7zip --version 21.7 --confirm
+        }
+
+        AfterAll {
+            $null = Invoke-Choco uninstall 7zip 7zip.install --confirm
+        }
+
+        It "Exits with Success (0)" {
+            $Output.ExitCode | Should -Be 0 -Because $Output.String
+        }
+
+        It "Upgrades version <OldVersion> of the package <Name>" -ForEach @(
+            @{ Name = "7zip"; OldVersion = "16.04" }
+            @{ Name = "7zip.install"; OldVersion = "16.04" }
+        ) {
+            "$env:ChocolateyInstall\lib\$Name\$Name.nuspec" | Should -Exist
+            [xml]$XML = Get-Content "$env:ChocolateyInstall\lib\$Name\$Name.nuspec"
+            $XML.package.metadata.version | Should -Not -Be $OldVersion
+        }
+
+        It "Have not upgraded dependency <Name>" {
+            "$env:ChocolateyInstall\lib\chocolatey-core.extension\chocolatey-core.extension.nupkg" | Should -Exist
+            [xml]$XML = Get-Content "$env:ChocolateyInstall\lib\chocolatey-core.extension\chocolatey-core.extension.nuspec"
+            $XML.package.metadata.id | Should -Be 'chocolatey-core.extension'
+            $XML.package.metadata.version | Should -Be '1.3.3'
+        }
+
+        It "Have not upgraded side by side installation of <Name> v<Version>" -ForEach @(
+            @{ Name = "chocolatey-core.extension"; Version = "1.3.5.1" }
+        ) {
+            "$env:ChocolateyInstall\lib\$Name.$Version\$Name.$Version.nupkg" | Should -Exist
+            [xml]$XML = Get-Content "$env:ChocolateyInstall\lib\$Name.$Version\$Name.$Version.nuspec"
+            $XML.package.metadata.id | Should -Be $Name
+            $XML.package.metadata.version | Should -Be $Version
+        }
+
+        It "Outputs a message showing that upgrading was successful" {
+            $Output.String | SHould -Match "Chocolatey upgraded 2/2 packages\."
+        }
+    }
+
+
+    Context "Can upgrade packages with dependencies containing outdated side by side installations and up to date dependency" {
+        BeforeAll {
+            Restore-ChocolateyInstallSnapshot
+
+            $null = Invoke-Choco install chocolatey-core.extension --version 1.3.3 --confirm
+            $null = Invoke-Choco install 7zip --version 16.04 --confirm
+            $null = Invoke-Choco install chocolatey-core.extension --version 1.3.0 --sxs --confirm
+
+            $Output = Invoke-Choco upgrade 7zip --version 21.7 --confirm
+        }
+
+        AfterAll {
+            $null = Invoke-Choco uninstall 7zip 7zip.install --confirm
+        }
+
+        It "Exits with Success (0)" {
+            $Output.ExitCode | Should -Be 0 -Because $Output.String
+        }
+
+        It "Upgrades version <OldVersion> of the package <Name>" -ForEach @(
+            @{ Name = "7zip"; OldVersion = "16.04" }
+            @{ Name = "7zip.install"; OldVersion = "16.04" }
+        ) {
+            "$env:ChocolateyInstall\lib\$Name\$Name.nuspec" | Should -Exist
+            [xml]$XML = Get-Content "$env:ChocolateyInstall\lib\$Name\$Name.nuspec"
+            $XML.package.metadata.version | Should -Not -Be $OldVersion
+        }
+
+        It "Have not upgraded dependency chocolatey-core.extension" {
+            "$env:ChocolateyInstall\lib\chocolatey-core.extension\chocolatey-core.extension.nupkg" | Should -Exist
+            [xml]$XML = Get-Content "$env:ChocolateyInstall\lib\chocolatey-core.extension\chocolatey-core.extension.nuspec"
+            $XML.package.metadata.id | Should -Be 'chocolatey-core.extension'
+            $XML.package.metadata.version | Should -Be '1.3.3'
+        }
+
+        It "Have not upgraded side by side installation of <Name> v<Version>" -ForEach @(
+            @{ Name = "chocolatey-core.extension"; Version = "1.3.0" }
+        ) {
+            "$env:ChocolateyInstall\lib\$Name.$Version\$Name.$Version.nupkg" | Should -Exist
+            [xml]$XML = Get-Content "$env:ChocolateyInstall\lib\$Name.$Version\$Name.$Version.nuspec"
+            $XML.package.metadata.id | Should -Be $Name
+            $XML.package.metadata.version | Should -Be $Version
+        }
+
+        It "Outputs a message showing that upgrading was successful" {
+            $Output.String | SHould -Match "Chocolatey upgraded 2/2 packages\."
+        }
+    }
+}