diff --git a/Invoke-Tests.ps1 b/Invoke-Tests.ps1
index d6ce96f030..6ff80f79bc 100644
--- a/Invoke-Tests.ps1
+++ b/Invoke-Tests.ps1
@@ -54,12 +54,53 @@ else {
 if (-not (Test-Path "$TestPath/packages") -or -not $SkipPackaging) {
     $null = New-Item -Path "$TestPath/packages" -ItemType Directory -Force
     # Get and pack packages
-    $nuspecs = Get-ChildItem -Path $PSScriptRoot/src/chocolatey.tests.integration, $PSScriptRoot/tests/packages -Recurse -Include *.nuspec | Where-Object FullName -notmatch 'bin'
+    $nuspecs = Get-ChildItem -Path $PSScriptRoot/src/chocolatey.tests.integration, $PSScriptRoot/tests/packages -Recurse -Include *.nuspec | Where-Object FullName -NotMatch 'bin'
     Get-ChildItem -Path $PSScriptRoot/tests/packages -Recurse -Include *.nupkg | Copy-Item -Destination "$TestPath/packages"
 
-    foreach ($file in $nuspecs) {
-        Write-Host "Packaging $file"
-        $null = choco pack $file.FullName --out "$TestPath/packages"
+    $packFailures = foreach ($file in $nuspecs) {
+        # Include allow-unofficial in case an unofficial Chocolatey has been installed globally for testing
+        $packOutput = choco pack $file.FullName --out "$TestPath/packages" --allow-unofficial
+        if ($LASTEXITCODE -ne 0) {
+            [pscustomobject]@{
+                Package = $file.FullName
+                ExitCode = $LASTEXITCODE
+                Output = $packOutput
+            }
+            Write-Warning "Failed to pack $file"
+        }
+        else {
+            Write-Host "Packaged $file"
+        }
+    }
+
+    if ($null -ne $packFailures) {
+        foreach ($failure in $packFailures) {
+            Write-Warning "$($failure.Package) failed to pack with exit code: $($failure.ExitCode)"
+            $failure.Output | Write-Warning
+        }
+        # If you want to stop things, change this to a throw.
+        # This is not currently throwing as there are two packages that are supposed to fail.
+        Write-Error "$($packFailures.Count) packages failed to pack."
+    }
+}
+
+if (-not (Test-Path "$TestPath/all-packages") -or -not $SkipPackaging) {
+    $null = New-Item -Path "$TestPath/all-packages" -ItemType Directory -Force
+
+    # These are the package ids that are loaded into the all packages test repository.
+    $AllPackagesRepository = @(
+        'isdependency'
+        'hasdependency'
+        'hasnesteddependency'
+        'downgradesdependency'
+        'dependencyfailure'
+        'hasfailingnesteddependency'
+        'failingdependency'
+        'isexactversiondependency'
+    )
+
+    foreach ($package in $AllPackagesRepository) {
+        $null = Copy-Item "$TestPath/packages/$package.*.nupkg" "$TestPath/all-packages/"
     }
 }
 
@@ -97,6 +138,7 @@ try {
 
     Import-Module $PSScriptRoot\tests\helpers\common-helpers.psm1 -Force
     $null = Invoke-Choco source add --name hermes --source "$TestPath/packages"
+    $null = Invoke-Choco source add --name hermes-all --source "$TestPath/all-packages"
     Enable-ChocolateyFeature -Name allowGlobalConfirmation
     $PesterConfiguration = [PesterConfiguration]@{
         Run        = @{
diff --git a/src/chocolatey/StringResources.cs b/src/chocolatey/StringResources.cs
index 8f04a3e641..e28c11eb75 100644
--- a/src/chocolatey/StringResources.cs
+++ b/src/chocolatey/StringResources.cs
@@ -56,5 +56,13 @@ public static class EnvironmentVariables
             [Browsable(false)]
             internal const string PackageNuspecVersion = "packageNuspecVersion";
         }
+
+        public static class ErrorMessages
+        {
+            [EditorBrowsable(EditorBrowsableState.Never)]
+            [Browsable(false)]
+            internal const string UnableToDowngrade = "A newer version of {0} (v{1}) is already installed.{2} Use --allow-downgrade or --force to attempt to install older versions.";
+            internal const string DependencyFailedToInstall = "Failed to install {0} because a previous dependency failed.";
+        }
     }
 }
\ No newline at end of file
diff --git a/src/chocolatey/infrastructure.app/services/NugetService.cs b/src/chocolatey/infrastructure.app/services/NugetService.cs
index 8b74d713ae..c701feb980 100644
--- a/src/chocolatey/infrastructure.app/services/NugetService.cs
+++ b/src/chocolatey/infrastructure.app/services/NugetService.cs
@@ -578,6 +578,12 @@ public virtual ConcurrentDictionary<string, PackageResult> Install(ChocolateyCon
 
             foreach (var packageName in packageNames.OrEmpty())
             {
+                if (packageResultsToReturn.ContainsKey(packageName))
+                {
+                    // We have already processed this package (likely during dependency resolution of another package).
+                    continue;
+                }
+                
                 // We need to ensure we are using a clean configuration file
                 // before we start reading it.
                 config.RevertChanges();
@@ -599,6 +605,7 @@ public virtual ConcurrentDictionary<string, PackageResult> Install(ChocolateyCon
                 if (installedPackage != null && (version == null || version == installedPackage.PackageMetadata.Version) && !config.Force)
                 {
                     var logMessage = "{0} v{1} already installed.{2} Use --force to reinstall, specify a version to install, or try upgrade.".FormatWith(installedPackage.Name, installedPackage.Version, Environment.NewLine);
+                    // We need a temporary PackageResult so that we can add to the Messages collection.
                     var nullResult = packageResultsToReturn.GetOrAdd(packageName, installedPackage);
                     nullResult.Messages.Add(new ResultMessage(ResultType.Warn, logMessage));
                     nullResult.Messages.Add(new ResultMessage(ResultType.Inconclusive, logMessage));
@@ -619,9 +626,9 @@ public virtual ConcurrentDictionary<string, PackageResult> Install(ChocolateyCon
 
                 if (installedPackage != null && version != null && version < installedPackage.PackageMetadata.Version && !config.AllowDowngrade)
                 {
-                    var logMessage = "A newer version of {0} (v{1}) is already installed.{2} Use --allow-downgrade or --force to attempt to install older versions.".FormatWith(installedPackage.Name, installedPackage.Version, Environment.NewLine);
-                    var nullResult = packageResultsToReturn.GetOrAdd(packageName, installedPackage);
-                    nullResult.Messages.Add(new ResultMessage(ResultType.Error, logMessage));
+                    var logMessage = StringResources.ErrorMessages.UnableToDowngrade.FormatWith(installedPackage.Name, installedPackage.Version, Environment.NewLine);
+                    packageResultsToReturn.GetOrAdd(packageName, installedPackage)
+                        .Messages.Add(new ResultMessage(ResultType.Error, logMessage));
                     this.Log().Error(ChocolateyLoggers.Important, logMessage);
                     continue;
                 }
@@ -793,6 +800,26 @@ Version was specified as '{0}'. It is possible that version
 
                 foreach (SourcePackageDependencyInfo packageDependencyInfo in resolvedPackages)
                 {
+                    // Don't attempt to action this package if dependencies failed.
+                    if (packageDependencyInfo != null && packageResultsToReturn.Any(r => r.Value.Success != true && packageDependencyInfo.Dependencies.Any(d => d.Id.Equals(r.Value.Identity.Id, StringComparison.OrdinalIgnoreCase))))
+                    {
+                        var logMessage = StringResources.ErrorMessages.DependencyFailedToInstall.FormatWith(packageDependencyInfo.Id);
+                        packageResultsToReturn
+                            .GetOrAdd(
+                                packageDependencyInfo.Id,
+                                new PackageResult(packageDependencyInfo.Id, packageDependencyInfo.Version.ToFullStringChecked(), string.Empty)
+                            )
+                            .Messages.Add(new ResultMessage(ResultType.Error, logMessage));
+                        this.Log().Error(ChocolateyLoggers.Important, logMessage);
+
+                        if (config.Features.StopOnFirstPackageFailure)
+                        {
+                            throw new ApplicationException("Stopping further execution as {0} has failed install.".FormatWith(packageDependencyInfo.Id));
+                        }
+
+                        continue;
+                    }
+
                     var packageRemoteMetadata = packagesToInstall.FirstOrDefault(p => p.Identity.Equals(packageDependencyInfo));
 
                     if (packageRemoteMetadata is null)
@@ -809,6 +836,22 @@ Version was specified as '{0}'. It is possible that version
                     var packageToUninstall = packagesToUninstall.FirstOrDefault(p => p.PackageMetadata.Id.Equals(packageDependencyInfo.Id, StringComparison.OrdinalIgnoreCase));
                     if (packageToUninstall != null)
                     {
+                        // Are we attempting a downgrade? We need to ensure it's allowed...
+                        if (!config.AllowDowngrade && packageToUninstall.Identity.HasVersion && packageDependencyInfo.HasVersion && packageDependencyInfo.Version < packageToUninstall.Identity.Version)
+                        {
+                            var logMessage = StringResources.ErrorMessages.UnableToDowngrade.FormatWith(packageToUninstall.Name, packageToUninstall.Version, Environment.NewLine);
+                            packageResultsToReturn.GetOrAdd(packageToUninstall.Name, packageToUninstall)
+                                .Messages.Add(new ResultMessage(ResultType.Error, logMessage));
+                            this.Log().Error(ChocolateyLoggers.Important, logMessage);
+                            
+                            if (config.Features.StopOnFirstPackageFailure)
+                            {
+                                throw new ApplicationException("Stopping further execution as {0} has failed install.".FormatWith(packageToUninstall.Identity.Id));
+                            }
+
+                            continue;
+                        }
+
                         shouldAddForcedResultMessage = true;
                         BackupAndRunBeforeModify(packageToUninstall, config, beforeModifyAction);
                         packageToUninstall.InstallLocation = pathResolver.GetInstallPath(packageToUninstall.Identity);
@@ -1051,6 +1094,12 @@ public virtual ConcurrentDictionary<string, PackageResult> Upgrade(ChocolateyCon
 
             foreach (var packageName in config.PackageNames.Split(new[] { ApplicationParameters.PackageNamesSeparator }, StringSplitOptions.RemoveEmptyEntries).OrEmpty())
             {
+                if (packageResultsToReturn.ContainsKey(packageName))
+                {
+                    // We have already processed this package (likely during dependency resolution of another package).
+                    continue;
+                }
+
                 // We need to ensure we are using a clean configuration file
                 // before we start reading it.
                 config.RevertChanges();
@@ -1138,9 +1187,9 @@ public virtual ConcurrentDictionary<string, PackageResult> Upgrade(ChocolateyCon
 
                 if (version != null && version < installedPackage.PackageMetadata.Version && !config.AllowDowngrade)
                 {
-                    var logMessage = "A newer version of {0} (v{1}) is already installed.{2} Use --allow-downgrade or --force to attempt to upgrade to older versions.".FormatWith(installedPackage.PackageMetadata.Id, installedPackage.Version, Environment.NewLine);
-                    var nullResult = packageResultsToReturn.GetOrAdd(packageName, new PackageResult(installedPackage.PackageMetadata, pathResolver.GetInstallPath(installedPackage.PackageMetadata.Id)));
-                    nullResult.Messages.Add(new ResultMessage(ResultType.Error, logMessage));
+                    var logMessage = StringResources.ErrorMessages.UnableToDowngrade.FormatWith(installedPackage.PackageMetadata.Id, installedPackage.Version, Environment.NewLine);
+                    packageResultsToReturn.GetOrAdd(packageName, new PackageResult(installedPackage.PackageMetadata, pathResolver.GetInstallPath(installedPackage.PackageMetadata.Id)))
+                        .Messages.Add(new ResultMessage(ResultType.Error, logMessage));
                     this.Log().Error(ChocolateyLoggers.Important, logMessage);
                     continue;
                 }
@@ -1559,6 +1608,25 @@ public virtual ConcurrentDictionary<string, PackageResult> Upgrade(ChocolateyCon
                                 break;
                             }
 
+                            // Don't attempt to action this package if dependencies failed.
+                            if (packageResultsToReturn.Any(r => r.Value.Success != true && packageDependencyInfo.Dependencies.Any(d => d.Id.Equals(r.Value.Identity.Id, StringComparison.OrdinalIgnoreCase))))
+                            {
+                                var logMessage = StringResources.ErrorMessages.DependencyFailedToInstall.FormatWith(packageDependencyInfo.Id, packageDependencyInfo.Version);
+                                packageResultsToReturn.GetOrAdd(
+                                        packageDependencyInfo.Id, 
+                                        new PackageResult(packageDependencyInfo.Id, packageDependencyInfo.Version.ToFullStringChecked(), string.Empty)
+                                    )
+                                    .Messages.Add(new ResultMessage(ResultType.Error, logMessage));
+                                this.Log().Error(ChocolateyLoggers.Important, logMessage);
+
+                                if (config.Features.StopOnFirstPackageFailure)
+                                {
+                                    throw new ApplicationException("Stopping further execution as {0} has failed.".FormatWith(packageDependencyInfo.Id));
+                                }
+
+                                continue;
+                            }
+
                             var packageRemoteMetadata = packagesToInstall.FirstOrDefault(p => p.Identity.Equals(packageDependencyInfo));
 
                             if (packageRemoteMetadata is null)
@@ -1576,6 +1644,32 @@ public virtual ConcurrentDictionary<string, PackageResult> Upgrade(ChocolateyCon
                             {
                                 if (packageToUninstall != null)
                                 {
+                                    // Are we attempting a downgrade? We need to ensure it's allowed...
+                                    if (!config.AllowDowngrade && packageToUninstall.Identity.HasVersion && packageDependencyInfo.HasVersion && packageDependencyInfo.Version < packageToUninstall.Identity.Version)
+                                    {
+                                        var logMessage = StringResources.ErrorMessages.UnableToDowngrade.FormatWith(packageToUninstall.Name, packageToUninstall.Version, Environment.NewLine);
+                                        packageResultsToReturn.GetOrAdd(packageToUninstall.Name, packageToUninstall)
+                                            .Messages.Add(new ResultMessage(ResultType.Error, logMessage));
+                                        this.Log().Error(ChocolateyLoggers.Important, logMessage);
+                                        
+                                        if (config.Features.StopOnFirstPackageFailure)
+                                        {
+                                            throw new ApplicationException("Stopping further execution as {0} has failed.".FormatWith(packageDependencyInfo.Id));
+                                        }
+
+                                        continue;
+                                    }
+
+                                    // Package was previously marked inconclusive (not upgraded). We need remove the message since we are now upgrading it.
+                                    // Packages that are inconclusive but successful are not labeled as successful at the end of the run.
+                                    var checkResult = packageResultsToReturn.GetOrAdd(packageToUninstall.Name, packageToUninstall);
+
+                                    while (checkResult.Inconclusive)
+                                    {
+                                        checkResult.Messages.Remove(checkResult.Messages.FirstOrDefault((m) => m.MessageType == ResultType.Inconclusive));
+                                    }
+
+
                                     var oldPkgInfo = _packageInfoService.Get(packageToUninstall.PackageMetadata);
 
                                     BackupAndRunBeforeModify(packageToUninstall, oldPkgInfo, config, beforeUpgradeAction);
diff --git a/tests/Vagrantfile b/tests/Vagrantfile
index a6bd2bf065..ceef065bc1 100644
--- a/tests/Vagrantfile
+++ b/tests/Vagrantfile
@@ -69,6 +69,7 @@ Vagrant.configure("2") do |config|
   config.vm.provision "shell", name: "clear-packages", inline: <<-SHELL
     Write-Host "($(Get-Date -Format "dddd MM/dd/yyyy HH:mm:ss K")) Clearing the packages directory"
     Remove-Item "$env:TEMP/chocolateyTests/packages" -Recurse -Force -ErrorAction SilentlyContinue
+    Remove-Item "$env:TEMP/chocolateyTests/all-packages" -Recurse -Force -ErrorAction SilentlyContinue
   SHELL
   config.vm.provision "shell", name: "test", inline: <<-SHELL
     # Copy changed files.
diff --git a/tests/helpers/common/Chocolatey/Get-ChocolateyInstalledPackages.ps1 b/tests/helpers/common/Chocolatey/Get-ChocolateyInstalledPackages.ps1
new file mode 100644
index 0000000000..0881ab2bc6
--- /dev/null
+++ b/tests/helpers/common/Chocolatey/Get-ChocolateyInstalledPackages.ps1
@@ -0,0 +1,3 @@
+function Get-ChocolateyInstalledPackages {
+    (Invoke-Choco list -r).Lines | ConvertFrom-ChocolateyOutput -Command List
+}
diff --git a/tests/packages/dependencyfailure/dependencyfailure.nuspec b/tests/packages/dependencyfailure/dependencyfailure.nuspec
new file mode 100644
index 0000000000..4ab6e842ad
--- /dev/null
+++ b/tests/packages/dependencyfailure/dependencyfailure.nuspec
@@ -0,0 +1,23 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
+  <metadata>
+    <id>dependencyfailure</id>
+    <version>1.0.0</version>
+    <title>dependencyfailure (Install)</title>
+    <authors>__REPLACE_AUTHORS_OF_SOFTWARE_COMMA_SEPARATED__</authors>
+    <projectUrl>https://_Software_Location_REMOVE_OR_FILL_OUT_</projectUrl>
+    <tags>dependencyfailure admin SPACE_SEPARATED</tags>
+    <summary>Package includes a dependency for a package that is known to fail installation.</summary>
+    <description>
+      Package includes a dependency for a package that is known to fail installation.
+
+      It can be used in tests to ensure that failing dependencies do not allow the package to install.
+    </description>
+    <dependencies>
+      <dependency id="failingdependency" version="1.0.0" />
+    </dependencies>
+  </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/tests/packages/dependencyfailure/tools/chocolateyinstall.ps1 b/tests/packages/dependencyfailure/tools/chocolateyinstall.ps1
new file mode 100644
index 0000000000..719bcd8ac7
--- /dev/null
+++ b/tests/packages/dependencyfailure/tools/chocolateyinstall.ps1
@@ -0,0 +1 @@
+Write-Host "I'm successful!"
\ No newline at end of file
diff --git a/tests/packages/failingdependency/failingdependency.nuspec b/tests/packages/failingdependency/failingdependency.nuspec
new file mode 100644
index 0000000000..c8179b5e80
--- /dev/null
+++ b/tests/packages/failingdependency/failingdependency.nuspec
@@ -0,0 +1,16 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
+  <metadata>
+    <id>failingdependency</id>
+    <version>1.0.0</version>
+    <title>dependencyfailure (Install)</title>
+    <authors>__REPLACE_AUTHORS_OF_SOFTWARE_COMMA_SEPARATED__</authors>
+    <projectUrl>https://_Software_Location_REMOVE_OR_FILL_OUT_</projectUrl>
+    <tags>dependencyfailure admin SPACE_SEPARATED</tags>
+    <summary>Package that fails to install. Used as part of dependency tree.</summary>
+    <description>Package that fails to install. Used as part of dependency tree.</description>
+  </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/tests/packages/failingdependency/tools/chocolateyinstall.ps1 b/tests/packages/failingdependency/tools/chocolateyinstall.ps1
new file mode 100644
index 0000000000..04105d6173
--- /dev/null
+++ b/tests/packages/failingdependency/tools/chocolateyinstall.ps1
@@ -0,0 +1,2 @@
+Write-Error "This should fail!"
+$env:ChocolateyExitCode = '15608'
diff --git a/tests/packages/get-chocolateyunzip-licensed/get-chocolateyunzip-licensed.nuspec b/tests/packages/get-chocolateyunzip-licensed/get-chocolateyunzip-licensed.nuspec
index a1daaef7c5..5370f474a7 100755
--- a/tests/packages/get-chocolateyunzip-licensed/get-chocolateyunzip-licensed.nuspec
+++ b/tests/packages/get-chocolateyunzip-licensed/get-chocolateyunzip-licensed.nuspec
@@ -1,59 +1,23 @@
 <?xml version="1.0" encoding="utf-8"?>
-<!-- Read this before creating packages: https://docs.chocolatey.org/en-us/create/create-packages -->
-<!-- It is especially important to read the above link to understand additional requirements when publishing packages to the community feed aka dot org (https://chocolatey.org/packages). -->
-<!-- Test your packages in a test environment: https://github.com/chocolatey/chocolatey-test-environment -->
-
-<!--
-This is a nuspec. It mostly adheres to https://docs.nuget.org/create/Nuspec-Reference. Chocolatey uses a special version of NuGet.Core that allows us to do more than was initially possible. As such there are certain things to be aware of:
-
-* the package xmlns schema url may cause issues with nuget.exe
-* Any of the following elements can ONLY be used by choco tools - projectSourceUrl, docsUrl, mailingListUrl, bugTrackerUrl, packageSourceUrl, provides, conflicts, replaces
-* nuget.exe can still install packages with those elements but they are ignored. Any authoring tools or commands will error on those elements
--->
-<!-- You can embed software files directly into packages, as long as you are not bound by distribution rights. -->
-<!-- * If you are an organization making private packages, you probably have no issues here -->
-<!-- * If you are releasing to the community feed, you need to consider distribution rights. -->
 <!-- Do not remove this test for UTF-8: if “Ω” doesn’t appear as greek uppercase omega letter enclosed in quotation marks, you should use an editor that supports UTF-8, not this one. -->
-
 <package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
   <metadata>
-    <!-- == PACKAGE SPECIFIC SECTION == -->
-    <!-- This section is about this package, although id and version have ties back to the software -->
-    <!-- id is lowercase and if you want a good separator for words, use '-', not '.'. Dots are only acceptable as suffixes for certain types of packages, e.g. .install, .portable, .extension, .template -->
-    <!-- If the software is cross-platform, attempt to use the same id as the debian/rpm package(s) if possible. -->
     <id>get-chocolateyunzip-licensed</id>
-    <!-- version should MATCH as closely as possible with the underlying software -->
-    <!-- Is the version a prerelease of a version? https://docs.nuget.org/create/versioning#creating-prerelease-packages -->
-    <!-- Note that unstable versions like 0.0.1 can be considered a released version, but it's possible that one can release a 0.0.1-beta before you release a 0.0.1 version. If the version number is final, that is considered a released version and not a prerelease. -->
     <version>3.21.2</version>
-    <!-- owners is a poor name for maintainers of the package. It sticks around by this name for compatibility reasons. It basically means you. -->
-    <owners>__REPLACE__</owners>
-    <!-- ============================== -->
-
-    <!-- == SOFTWARE SPECIFIC SECTION == -->
-    <!-- This section is about the software itself -->
-    <title>__REPLACE__ (Portable)</title>
-    <authors>__REPLACE__</authors>
+    <owners>chocolatey</owners>
+    <title>get-chocolateyunzip-licensed (Portable)</title>
+    <authors>Chocolatey Software</authors>
     <!-- copyright is usually years and software vendor, but not required for internal feeds -->
-    <copyright>__REPLACE__</copyright>
+    <copyright>Chocolatey Software</copyright>
     <tags>get-chocolateyunzip-licensed</tags>
-    <description>__REPLACE__MarkDown_Okay</description>
-    <!-- =============================== -->
+    <description>
+      This package contains a commercial edition of the cmdlet `Get-ChocolateyUnzip`, and can be used to verify that installation with that cmdlet works as intended.
 
-    <!-- Specifying dependencies and version ranges? https://docs.nuget.org/create/versioning#specifying-version-ranges-in-.nuspec-files -->
-    <!--<dependencies>
-      <dependency id="" version="__MINIMUM_VERSION__" />
-      <dependency id="" version="[__EXACT_VERSION__]" />
-      <dependency id="" version="[_MIN_VERSION_INCLUSIVE, MAX_VERSION_INCLUSIVE]" />
-      <dependency id="" version="[_MIN_VERSION_INCLUSIVE, MAX_VERSION_EXCLUSIVE)" />
-      <dependency id="" />
-    </dependencies>-->
+Additionally it can be tested that the package will fail if being installed on FOSS Edition of Chocolatey.
 
-    <!--<provides>NOT YET IMPLEMENTED</provides>-->
-    <!--<conflicts>NOT YET IMPLEMENTED</conflicts>-->
-    <!--<replaces>NOT YET IMPLEMENTED</replaces>-->
+The package defines the license types `business`, `Education` and `professional` as being valid licenses.
+    </description>
   </metadata>
-  <!-- this section controls what actually gets packaged into the Chocolatey package -->
   <files>
     <file src="tools\**" target="tools" />
   </files>
diff --git a/tests/packages/hasfailingnesteddependency/1.0.0/hasfailingnesteddependency.nuspec b/tests/packages/hasfailingnesteddependency/1.0.0/hasfailingnesteddependency.nuspec
new file mode 100644
index 0000000000..6f13009705
--- /dev/null
+++ b/tests/packages/hasfailingnesteddependency/1.0.0/hasfailingnesteddependency.nuspec
@@ -0,0 +1,27 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2010/07/nuspec.xsd">
+    <metadata>
+        <id>hasfailingnesteddependency</id>
+        <version>1.0.0</version>
+        <title>hasfailingnesteddependency</title>
+        <authors>Chocolatey Software</authors>
+        <owners>chocolatey</owners>
+        <requireLicenseAcceptance>false</requireLicenseAcceptance>
+        <description>
+          Package that contains dependencies that have dependencies that may fail to install.
+
+          Used for testing dependency resolution and ensuring dependency failures do not allow package installation.
+        </description>
+        <summary>Package that contains dependencies that have dependencies that may fail to install.</summary>
+        <releaseNotes />
+        <copyright />
+        <tags>hasfailingnesteddependency admin</tags>
+        <dependencies>
+            <dependency id="dependencyfailure" version="1.0.0" />
+            <dependency id="downgradesdependency" version="2.0.0" />
+        </dependencies>
+    </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/tests/packages/hasfailingnesteddependency/1.0.0/tools/chocolateyinstall.ps1 b/tests/packages/hasfailingnesteddependency/1.0.0/tools/chocolateyinstall.ps1
new file mode 100644
index 0000000000..d64eb8f47b
--- /dev/null
+++ b/tests/packages/hasfailingnesteddependency/1.0.0/tools/chocolateyinstall.ps1
@@ -0,0 +1 @@
+Write-Output "$env:PackageName $env:PackageVersion Installed"
\ No newline at end of file
diff --git a/tests/packages/hasfailingnesteddependency/1.0.0/tools/chocolateyuninstall.ps1 b/tests/packages/hasfailingnesteddependency/1.0.0/tools/chocolateyuninstall.ps1
new file mode 100644
index 0000000000..9ead91ffa3
--- /dev/null
+++ b/tests/packages/hasfailingnesteddependency/1.0.0/tools/chocolateyuninstall.ps1
@@ -0,0 +1 @@
+Write-Output "$env:PackageName $env:PackageVersion Uninstalled"
\ No newline at end of file
diff --git a/tests/packages/hasnesteddependency/1.0.0/hasnesteddependency.nuspec b/tests/packages/hasnesteddependency/1.0.0/hasnesteddependency.nuspec
new file mode 100644
index 0000000000..fbc8d2df82
--- /dev/null
+++ b/tests/packages/hasnesteddependency/1.0.0/hasnesteddependency.nuspec
@@ -0,0 +1,22 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2010/07/nuspec.xsd">
+    <metadata>
+        <id>hasnesteddependency</id>
+        <version>1.0.0</version>
+        <title>hasnesteddependency</title>
+        <authors>Chocolatey Software</authors>
+        <owners>chocolatey</owners>
+        <requireLicenseAcceptance>false</requireLicenseAcceptance>
+        <description>Package used for testing nested dependencies.</description>
+        <summary>Package used for testing nested dependencies.</summary>
+        <releaseNotes />
+        <copyright />
+        <tags>hasnesteddependency admin</tags>
+        <dependencies>
+            <dependency id="hasdependency" version="1.0.0" />
+        </dependencies>
+    </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/tests/packages/hasnesteddependency/1.0.0/tools/chocolateyinstall.ps1 b/tests/packages/hasnesteddependency/1.0.0/tools/chocolateyinstall.ps1
new file mode 100644
index 0000000000..d64eb8f47b
--- /dev/null
+++ b/tests/packages/hasnesteddependency/1.0.0/tools/chocolateyinstall.ps1
@@ -0,0 +1 @@
+Write-Output "$env:PackageName $env:PackageVersion Installed"
\ No newline at end of file
diff --git a/tests/packages/hasnesteddependency/1.0.0/tools/chocolateyuninstall.ps1 b/tests/packages/hasnesteddependency/1.0.0/tools/chocolateyuninstall.ps1
new file mode 100644
index 0000000000..9ead91ffa3
--- /dev/null
+++ b/tests/packages/hasnesteddependency/1.0.0/tools/chocolateyuninstall.ps1
@@ -0,0 +1 @@
+Write-Output "$env:PackageName $env:PackageVersion Uninstalled"
\ No newline at end of file
diff --git a/tests/packages/test-chocolateypath/test-chocolateypath.nuspec b/tests/packages/test-chocolateypath/test-chocolateypath.nuspec
index 9756ecb9c7..580a48463b 100644
--- a/tests/packages/test-chocolateypath/test-chocolateypath.nuspec
+++ b/tests/packages/test-chocolateypath/test-chocolateypath.nuspec
@@ -1,81 +1,17 @@
 <?xml version="1.0" encoding="utf-8"?>
-<!-- Read this before creating packages: https://docs.chocolatey.org/en-us/create/create-packages -->
-<!-- It is especially important to read the above link to understand additional requirements when publishing packages to the community feed aka dot org (https://community.chocolatey.org/packages). -->
-
-<!-- Test your packages in a test environment: https://github.com/chocolatey/chocolatey-test-environment -->
-
-<!--
-This is a nuspec. It mostly adheres to https://docs.nuget.org/create/Nuspec-Reference. Chocolatey uses a special version of NuGet.Core that allows us to do more than was initially possible. As such there are certain things to be aware of:
-
-* the package xmlns schema url may cause issues with nuget.exe
-* Any of the following elements can ONLY be used by choco tools - projectSourceUrl, docsUrl, mailingListUrl, bugTrackerUrl, packageSourceUrl, provides, conflicts, replaces
-* nuget.exe can still install packages with those elements but they are ignored. Any authoring tools or commands will error on those elements
--->
-
-<!-- You can embed software files directly into packages, as long as you are not bound by distribution rights. -->
-<!-- * If you are an organization making private packages, you probably have no issues here -->
-<!-- * If you are releasing to the community feed, you need to consider distribution rights. -->
 <!-- Do not remove this test for UTF-8: if “Ω” doesn’t appear as greek uppercase omega letter enclosed in quotation marks, you should use an editor that supports UTF-8, not this one. -->
 <package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
   <metadata>
-    <!-- == PACKAGE SPECIFIC SECTION == -->
-    <!-- This section is about this package, although id and version have ties back to the software -->
-    <!-- id is lowercase and if you want a good separator for words, use '-', not '.'. Dots are only acceptable as suffixes for certain types of packages, e.g. .install, .portable, .extension, .template -->
-    <!-- If the software is cross-platform, attempt to use the same id as the debian/rpm package(s) if possible. -->
     <id>test-chocolateypath</id>
-    <!-- version should MATCH as closely as possible with the underlying software -->
-    <!-- Is the version a prerelease of a version? https://docs.nuget.org/create/versioning#creating-prerelease-packages -->
-    <!-- Note that unstable versions like 0.0.1 can be considered a released version, but it's possible that one can release a 0.0.1-beta before you release a 0.0.1 version. If the version number is final, that is considered a released version and not a prerelease. -->
     <version>0.1.0</version>
-    <!-- <packageSourceUrl>Where is this Chocolatey package located (think GitHub)? packageSourceUrl is highly recommended for the community feed</packageSourceUrl>-->
-    <!-- owners is a poor name for maintainers of the package. It sticks around by this name for compatibility reasons. It basically means you. -->
-    <!--<owners>__REPLACE_YOUR_NAME__</owners>-->
-    <!-- ============================== -->
-
-    <!-- == SOFTWARE SPECIFIC SECTION == -->
-    <!-- This section is about the software itself -->
     <title>test-packagepath (Install)</title>
     <authors>__REPLACE_AUTHORS_OF_SOFTWARE_COMMA_SEPARATED__</authors>
-    <!-- projectUrl is required for the community feed -->
     <projectUrl>https://_Software_Location_REMOVE_OR_FILL_OUT_</projectUrl>
-    <!-- There are a number of CDN Services that can be used for hosting the Icon for a package. More information can be found here: https://docs.chocolatey.org/en-us/create/create-packages#package-icon-guidelines -->
-    <!-- Here is an example using Githack -->
-    <!--<iconUrl>http://rawcdn.githack.com/__REPLACE_YOUR_REPO__/master/icons/test-packagepath.png</iconUrl>-->
-    <!-- <copyright>Year Software Vendor</copyright> -->
-    <!-- If there is a license Url available, it is required for the community feed -->
-    <!-- <licenseUrl>Software License Location __REMOVE_OR_FILL_OUT__</licenseUrl>
-    <requireLicenseAcceptance>true</requireLicenseAcceptance>-->
-    <!--<projectSourceUrl>Software Source Location - is the software FOSS somewhere? Link to it with this</projectSourceUrl>-->
-    <!--<docsUrl>At what url are the software docs located?</docsUrl>-->
-    <!--<mailingListUrl></mailingListUrl>-->
-    <!--<bugTrackerUrl></bugTrackerUrl>-->
     <tags>test-packagepath SPACE_SEPARATED</tags>
-    <summary>__REPLACE__</summary>
-    <description>__REPLACE__MarkDown_Okay </description>
-    <!-- <releaseNotes>__REPLACE_OR_REMOVE__MarkDown_Okay</releaseNotes> -->
-    <!-- =============================== -->
-
-    <!-- Specifying dependencies and version ranges? https://docs.nuget.org/create/versioning#specifying-version-ranges-in-.nuspec-files -->
-    <!--<dependencies>
-      <dependency id="" version="__MINIMUM_VERSION__" />
-      <dependency id="" version="[__EXACT_VERSION__]" />
-      <dependency id="" version="[_MIN_VERSION_INCLUSIVE, MAX_VERSION_INCLUSIVE]" />
-      <dependency id="" version="[_MIN_VERSION_INCLUSIVE, MAX_VERSION_EXCLUSIVE)" />
-      <dependency id="" />
-      <dependency id="chocolatey-core.extension" version="1.1.0" />
-    </dependencies>-->
-    <!-- chocolatey-core.extension - https://community.chocolatey.org/packages/chocolatey-core.extension
-         - You want to use Get-UninstallRegistryKey on less than 0.9.10 (in chocolateyUninstall.ps1)
-         - You want to use Get-PackageParameters and on less than 0.11.0
-         - You want to take advantage of other functions in the core community maintainer's team extension package
-    -->
-
-    <!--<provides>NOT YET IMPLEMENTED</provides>-->
-    <!--<conflicts>NOT YET IMPLEMENTED</conflicts>-->
-    <!--<replaces>NOT YET IMPLEMENTED</replaces>-->
+    <summary>Package to test the Get-ChocolateyPath Chocolatey PowerShell function.</summary>
+    <description>Package to test the Get-ChocolateyPath Chocolatey PowerShell function.</description>
   </metadata>
   <files>
-    <!-- this section controls what actually gets packaged into the Chocolatey package -->
     <file src="tools\**" target="tools" />
   </files>
 </package>
diff --git a/tests/packages/upgradedowngradesdependency/1.0.0/downgradesdependency.nuspec b/tests/packages/upgradedowngradesdependency/1.0.0/downgradesdependency.nuspec
new file mode 100644
index 0000000000..0ad0f09d93
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/1.0.0/downgradesdependency.nuspec
@@ -0,0 +1,29 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2010/07/nuspec.xsd">
+    <metadata>
+        <id>downgradesdependency</id>
+        <version>1.0.0</version>
+        <title>Has out of range Dependency</title>
+        <authors>Chocolatey Software</authors>
+        <owners>chocolatey</owners>
+        <requireLicenseAcceptance>false</requireLicenseAcceptance>
+        <description>
+          These packages can be used to test the installation or upgrading of packages that require an existing package to downgrade.
+
+Each version is available as `upgradedowngradesdependency` and `downgradesdependency`. This is to allow testing of scenarios where `choco upgrade all` would process the dependency before and after the parent package.
+
+- Version 1.0.0 contains a range that can be used in an upgrade scenario and has a dependency on `isdependency 1.0.0 or greater`
+- Version 2.0.0 contains an exact dependency on `isdependency` with a version of `1.0.0`
+        </description>
+        <summary>Package to test for out of range dependencies. This 1st version have a valid exact range.</summary>
+        <releaseNotes />
+        <copyright />
+        <tags>upgradedowngradesdependency admin</tags>
+        <dependencies>
+            <dependency id="isdependency" version="[1.0.0,)" />
+        </dependencies>
+    </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateybeforemodify.ps1 b/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateybeforemodify.ps1
new file mode 100644
index 0000000000..7d0b91fece
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateybeforemodify.ps1
@@ -0,0 +1 @@
+Write-Output "Upgrading or Uninstalling $env:PackageName $env:PackageVersion"
\ No newline at end of file
diff --git a/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateyinstall.ps1 b/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateyinstall.ps1
new file mode 100644
index 0000000000..d64eb8f47b
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateyinstall.ps1
@@ -0,0 +1 @@
+Write-Output "$env:PackageName $env:PackageVersion Installed"
\ No newline at end of file
diff --git a/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateyuninstall.ps1 b/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateyuninstall.ps1
new file mode 100644
index 0000000000..9ead91ffa3
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/1.0.0/tools/chocolateyuninstall.ps1
@@ -0,0 +1 @@
+Write-Output "$env:PackageName $env:PackageVersion Uninstalled"
\ No newline at end of file
diff --git a/tests/packages/upgradedowngradesdependency/1.0.0/upgradedowngradesdependency.nuspec b/tests/packages/upgradedowngradesdependency/1.0.0/upgradedowngradesdependency.nuspec
new file mode 100644
index 0000000000..bb723ce36e
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/1.0.0/upgradedowngradesdependency.nuspec
@@ -0,0 +1,29 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2010/07/nuspec.xsd">
+    <metadata>
+        <id>upgradedowngradesdependency</id>
+        <version>1.0.0</version>
+        <title>Has out of range Dependency</title>
+        <authors>Chocolatey Software</authors>
+        <owners>chocolatey</owners>
+        <requireLicenseAcceptance>false</requireLicenseAcceptance>
+        <description>
+          These packages can be used to test the installation or upgrading of packages that require an existing package to downgrade.
+
+Each version is available as `upgradedowngradesdependency` and `downgradesdependency`. This is to allow testing of scenarios where `choco upgrade all` would process the dependency before and after the parent package.
+
+- Version 1.0.0 contains a range that can be used in an upgrade scenario and has a dependency on `isdependency 1.0.0 or greater`
+- Version 2.0.0 contains an exact dependency on `isdependency` with a version of `1.0.0`
+        </description>
+        <summary>Package to test for out of range dependencies. This 1st version have a valid exact range.</summary>
+        <releaseNotes />
+        <copyright />
+        <tags>upgradedowngradesdependency admin</tags>
+        <dependencies>
+            <dependency id="isdependency" version="[1.0.0,)" />
+        </dependencies>
+    </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/tests/packages/upgradedowngradesdependency/2.0.0/downgradesdependency.nuspec b/tests/packages/upgradedowngradesdependency/2.0.0/downgradesdependency.nuspec
new file mode 100644
index 0000000000..efccc67761
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/2.0.0/downgradesdependency.nuspec
@@ -0,0 +1,29 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2010/07/nuspec.xsd">
+    <metadata>
+        <id>downgradesdependency</id>
+        <version>2.0.0</version>
+        <title>Has out of range Dependency (Below available)</title>
+        <authors>Chocolatey Software</authors>
+        <owners>chocolatey</owners>
+        <requireLicenseAcceptance>false</requireLicenseAcceptance>
+        <description>
+          These packages can be used to test the installation or upgrading of packages that require an existing package to downgrade.
+
+Each version is available as `upgradedowngradesdependency` and `downgradesdependency`. This is to allow testing of scenarios where `choco upgrade all` would process the dependency before and after the parent package.
+
+- Version 1.0.0 contains a range that can be used in an upgrade scenario and has a dependency on `isdependency 1.0.0 or greater`
+- Version 2.0.0 contains an exact dependency on `isdependency` with a version of `1.0.0`
+        </description>
+        <summary>Package to test for out of range dependencies. This version uses a dependency that require a lower version.</summary>
+        <releaseNotes />
+        <copyright />
+        <tags>upgradedowngradesdependency admin</tags>
+        <dependencies>
+            <dependency id="isdependency" version="[1.0.0]" />
+        </dependencies>
+    </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateybeforemodify.ps1 b/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateybeforemodify.ps1
new file mode 100644
index 0000000000..7d0b91fece
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateybeforemodify.ps1
@@ -0,0 +1 @@
+Write-Output "Upgrading or Uninstalling $env:PackageName $env:PackageVersion"
\ No newline at end of file
diff --git a/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateyinstall.ps1 b/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateyinstall.ps1
new file mode 100644
index 0000000000..d64eb8f47b
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateyinstall.ps1
@@ -0,0 +1 @@
+Write-Output "$env:PackageName $env:PackageVersion Installed"
\ No newline at end of file
diff --git a/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateyuninstall.ps1 b/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateyuninstall.ps1
new file mode 100644
index 0000000000..9ead91ffa3
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/2.0.0/tools/chocolateyuninstall.ps1
@@ -0,0 +1 @@
+Write-Output "$env:PackageName $env:PackageVersion Uninstalled"
\ No newline at end of file
diff --git a/tests/packages/upgradedowngradesdependency/2.0.0/upgradedowngradesdependency.nuspec b/tests/packages/upgradedowngradesdependency/2.0.0/upgradedowngradesdependency.nuspec
new file mode 100644
index 0000000000..e00f3c9dea
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/2.0.0/upgradedowngradesdependency.nuspec
@@ -0,0 +1,29 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2010/07/nuspec.xsd">
+    <metadata>
+        <id>upgradedowngradesdependency</id>
+        <version>2.0.0</version>
+        <title>Has out of range Dependency (Below available)</title>
+        <authors>Chocolatey Software</authors>
+        <owners>chocolatey</owners>
+        <requireLicenseAcceptance>false</requireLicenseAcceptance>
+        <description>
+          These packages can be used to test the installation or upgrading of packages that require an existing package to downgrade.
+
+Each version is available as `upgradedowngradesdependency` and `downgradesdependency`. This is to allow testing of scenarios where `choco upgrade all` would process the dependency before and after the parent package.
+
+- Version 1.0.0 contains a range that can be used in an upgrade scenario and has a dependency on `isdependency 1.0.0 or greater`
+- Version 2.0.0 contains an exact dependency on `isdependency` with a version of `1.0.0`
+        </description>
+        <summary>Package to test for out of range dependencies. This version uses a dependency that require a lower version.</summary>
+        <releaseNotes />
+        <copyright />
+        <tags>upgradedowngradesdependency admin</tags>
+        <dependencies>
+            <dependency id="isdependency" version="[1.0.0]" />
+        </dependencies>
+    </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/tests/packages/upgradedowngradesdependency/Readme.md b/tests/packages/upgradedowngradesdependency/Readme.md
new file mode 100644
index 0000000000..0f2c4f806f
--- /dev/null
+++ b/tests/packages/upgradedowngradesdependency/Readme.md
@@ -0,0 +1,6 @@
+These packages can be used to test the installation or upgrading of packages that require an existing package to downgrade.
+
+Each version is available as `upgradedowngradesdependency` and `downgradesdependency`. This is to allow testing of scenarios where `choco upgrade all` would process the dependency before and after the parent package.
+
+- Version 1.0.0 contains a range that can be used in an upgrade scenario and has a dependency on `isdependency 1.0.0 or greater`
+- Version 2.0.0 contains an exact dependency on `isdependency` with a version of `1.0.0`
diff --git a/tests/pester-tests/commands/choco-install.Tests.ps1 b/tests/pester-tests/commands/choco-install.Tests.ps1
index 9cfa0f1a95..cbac68a900 100644
--- a/tests/pester-tests/commands/choco-install.Tests.ps1
+++ b/tests/pester-tests/commands/choco-install.Tests.ps1
@@ -217,7 +217,8 @@
         It "Should mention that package hash verification was skipped since local folder source is being used" {
             if ((Test-HasNuGetV3Source) -or (-not $env:TEST_KITCHEN)) {
                 $Output.Lines | Should -Contain "Source does not provide a package hash, skipping package hash validation." -Because $Output.String
-            } else {
+            }
+            else {
                 $Output.Lines | Should -Contain "Package hash matches expected hash." -Because $Output.String
             }
         }
@@ -1690,7 +1691,7 @@ To install a local, or remote file, you may use:
 
             $PackageUnderTest = "installpackage", "packagewithscript"
 
-            $Output = "a`n"*2 | Invoke-Choco install @PackageUnderTest
+            $Output = "a`n" * 2 | Invoke-Choco install @PackageUnderTest
         }
 
         It "Installs successfully and exits with success (0)" {
@@ -1740,7 +1741,8 @@ To install a local, or remote file, you may use:
         It 'Outputs download completed' {
             $testMessage = if ($features.License) {
                 "Download of 'cmake-3.21.2-windows-x86_64.zip' (36.01 MB) completed."
-            } else {
+            }
+            else {
                 "Download of cmake-3.21.2-windows-x86_64.zip (36.01 MB) completed."
             }
             $Output.Lines | Should -Contain $testMessage -Because $Output.String
@@ -1749,7 +1751,8 @@ To install a local, or remote file, you may use:
         It 'Outputs extracting correct archive' {
             $testMessage = if ($features.License) {
                 "Extracting cmake-3.21.2-windows-x86_64.zip to $env:ChocolateyInstall\lib\install-chocolateyzip\tools..."
-            } else {
+            }
+            else {
                 "Extracting $($paths.CachePathLong)\install-chocolateyzip\3.21.2\cmake-3.21.2-windows-x86_64.zip to $env:ChocolateyInstall\lib\install-chocolateyzip\tools..."
             }
             $Output.Lines | Should -Contain $testMessage -Because $Output.String
@@ -1925,8 +1928,8 @@ To install a local, or remote file, you may use:
     }
 
     Context "Installing a package with a non-normalized version number" -ForEach @(
-        @{ ExpectedPackageVersion = '1.0.0' ; SearchVersion = '1' ; NuspecVersion = '01.0.0.0'}
-        @{ ExpectedPackageVersion = '1.0.0' ; SearchVersion = '1.0' ; NuspecVersion = '01.0.0.0'}
+        @{ ExpectedPackageVersion = '1.0.0' ; SearchVersion = '1' ; NuspecVersion = '01.0.0.0' }
+        @{ ExpectedPackageVersion = '1.0.0' ; SearchVersion = '1.0' ; NuspecVersion = '01.0.0.0' }
         @{ ExpectedPackageVersion = '1.0.0' ; SearchVersion = '1.0.0' ; NuspecVersion = '01.0.0.0' }
         @{ ExpectedPackageVersion = '4.0.1' ; SearchVersion = '4.0.1' ; NuspecVersion = '004.0.01.0' }
         @{ ExpectedPackageVersion = '1.0.0' ; SearchVersion = '01.0.0.0' ; NuspecVersion = '01.0.0.0' }
@@ -2027,21 +2030,21 @@ To install a local, or remote file, you may use:
         }
 
         It 'Outputs <Name> as <Value>' -ForEach @(@{
-            Name = 'chocolateyPackageVersion'
-            Value= '0.9.0'
-        }
-        @{
-            Name = 'packageVersion'
-            Value= '0.9.0'
-        }
-        @{
-            Name = 'chocolateyPackageNuspecVersion'
-            Value= '0.9'
-        }
-        @{
-            Name = 'packageNuspecVersion'
-            Value= '0.9'
-        }) {
+                Name  = 'chocolateyPackageVersion'
+                Value = '0.9.0'
+            }
+            @{
+                Name  = 'packageVersion'
+                Value = '0.9.0'
+            }
+            @{
+                Name  = 'chocolateyPackageNuspecVersion'
+                Value = '0.9'
+            }
+            @{
+                Name  = 'packageNuspecVersion'
+                Value = '0.9'
+            }) {
             $Output.Lines | Should -Contain "$Name=$Value"
         }
     }
@@ -2070,6 +2073,203 @@ To install a local, or remote file, you may use:
         }
     }
 
+    Context 'Installing a package with argument (<Argument>) should (<AllowsDowngrade>) downgrade an existing package dependency.' -Tag Downgrade -ForEach @(
+        @{
+            Argument        = '--force'
+            AllowsDowngrade = $true
+            ExpectedExit    = 0
+        }
+        @{
+            Argument        = '--allow-downgrade'
+            AllowsDowngrade = $true
+            ExpectedExit    = 0
+        }
+        @{
+            Argument        = ''
+            AllowsDowngrade = $false
+            ExpectedExit    = 1
+        }
+    ) {
+        BeforeAll {
+            $DependentPackage = @{
+                Name    = 'isdependency'
+                Version = '2.1.0'
+            }
+
+            Restore-ChocolateyInstallSnapshot
+
+            $Setup = Invoke-Choco install $DependentPackage.Name --version $DependentPackage.Version --confirm
+            $Output = Invoke-Choco install downgradesdependency --confirm $Argument
+            $Packages = Get-ChocolateyInstalledPackages
+        }
+
+        It "Exits correctly (<ExpectedExit>)" {
+            $Output.ExitCode | Should -Be $ExpectedExit -Because $Output.String
+        }
+
+        It "Reports that it can (<AllowsDowngrade>) downgrade isdependency" {
+            if ($AllowsDowngrade) {
+                $Output.Lines | Should -Contain 'Chocolatey installed 2/2 packages.' -Because $Output.String
+            }
+            else {
+                $Output.Lines | Should -Contain 'Chocolatey installed 0/2 packages. 2 packages failed.' -Because $Output.String
+            }
+
+            $Output.Lines | Should -Contain -Not:($AllowsDowngrade) "A newer version of $($DependentPackage.Name) (v$($DependentPackage.Version)) is already installed." -Because $Output.String
+            $Output.Lines | Should -Contain -Not:($AllowsDowngrade) 'Use --allow-downgrade or --force to attempt to install older versions.' -Because $Output.String
+        }
+
+        It "Should have the expected packages" {
+            if ($AllowsDowngrade) {
+                $Packages | where { $_.Name -eq $DependentPackage.Name -and $_.Version -eq '1.0.0' } | Should -Not -BeNullOrEmpty -Because "Packages: $Packages $($Output.String)"
+            }
+            else {
+                $Packages | where { $_.Name -eq $DependentPackage.Name -and $_.Version -eq $DependentPackage.Version } | Should -Not -BeNullOrEmpty -Because "Packages: $Packages $($Output.String)"
+            }
+        }
+    }
+
+    Context 'Installing a package with argument (<Argument>) and StopOnFirstPackageFailure enabled should (<AllowsDowngrade>) downgrade an existing package dependency and correctly handle installpackage.' -Tag Downgrade, StopOnFirstPackageFailure -ForEach @(
+        @{
+            Argument        = '--force'
+            AllowsDowngrade = $true
+            ExpectedExit    = 0
+        }
+        @{
+            Argument        = '--allow-downgrade'
+            AllowsDowngrade = $true
+            ExpectedExit    = 0
+        }
+        @{
+            Argument        = ''
+            AllowsDowngrade = $false
+            ExpectedExit    = 1
+        }
+    ) {
+        BeforeAll {
+            $DependentPackage = @{
+                Name    = 'isdependency'
+                Version = '2.1.0'
+            }
+
+            Restore-ChocolateyInstallSnapshot
+
+            $Setup = Invoke-Choco install $DependentPackage.Name --version $DependentPackage.Version --confirm
+            $null = Enable-ChocolateyFeature -Name StopOnFirstPackageFailure
+            $Output = Invoke-Choco install downgradesdependency installpackage --confirm $Argument
+            $Packages = Get-ChocolateyInstalledPackages
+        }
+
+        It "Exits correctly (<ExpectedExit>)" {
+            $Output.ExitCode | Should -Be $ExpectedExit -Because $Output.String
+        }
+
+        It "Reports that it can (<AllowsDowngrade>) downgrade isdependency" {
+            $Output.Lines | Should -Contain -Not:($AllowsDowngrade) "A newer version of $($DependentPackage.Name) (v$($DependentPackage.Version)) is already installed." -Because $Output.String
+            $Output.Lines | Should -Contain -Not:($AllowsDowngrade) 'Use --allow-downgrade or --force to attempt to install older versions.' -Because $Output.String
+        }
+
+        It "Should have the expected packages" {
+            if ($AllowsDowngrade) {
+                $Packages | where { $_.Name -eq $DependentPackage.Name -and $_.Version -eq '1.0.0' } | Should -Not -BeNullOrEmpty -Because "Packages: $Packages $($Output.String)"
+            }
+            else {
+                $Packages | where { $_.Name -eq $DependentPackage.Name -and $_.Version -eq $DependentPackage.Version } | Should -Not -BeNullOrEmpty -Because "Packages: $Packages $($Output.String)"
+            }
+        }
+    }
+
+    Context 'Installing a package (<PackageName>) with a failing nested dependency should not install the package with failing dependencies' -ForEach @(
+        @{
+            PackageName = 'dependencyfailure;downgradesdependency;failingdependency;hasdependency;hasfailingnesteddependency;hasnesteddependency;isdependency;isexactversiondependency'.Split(';')
+        }
+        @{
+            PackageName = @('packages.config')
+        }
+        @{
+            PackageName = @('all')
+        }
+    ) {
+        BeforeAll {
+
+            Restore-ChocolateyInstallSnapshot -SetWorkingDirectory
+
+            Copy-Item "$PSScriptRoot/failingnested.packages.config" './packages.config'
+            Disable-ChocolateySource -All
+            Enable-ChocolateySource -Name 'hermes-all'
+
+            $Output = Invoke-Choco install @PackageName --confirm
+            $Packages = Get-ChocolateyInstalledPackages
+        }
+
+        It "Exits correctly (15608)" {
+            # failingdependency exits with 15608, so Chocolatey exits with that.
+            $Output.ExitCode | Should -Be 15608 -Because $Output.String
+        }
+
+        It "Should have the expected packages" {
+            $ExpectedPackages = @(
+                "downgradesdependency"
+                "isdependency"
+                "isexactversiondependency"
+            )
+            $UnexpectedPackages = @(
+                'dependencyfailure'
+                "dependencyfailure"
+                'hasfailingnesteddependency'
+            )
+
+            foreach ($package in $ExpectedPackages) {
+                $Packages.Name | Should -Contain $package -Because "Package: $package $($Output.String)"
+            }
+
+            foreach ($package in $UnexpectedPackages) {
+                $Packages.Name | Should -Not -Contain $package -Because "Package: $package $($Output.String)"
+            }
+        }
+    }
+
+    Context 'Installing a package (<PackageName>) with a failing nested dependency should not install the package with failing dependencies' -ForEach @( @{ PackageName = 'hasfailingnesteddependency;hasnesteddependency' } ) {
+        BeforeAll {
+
+            Restore-ChocolateyInstallSnapshot -SetWorkingDirectory
+
+            Disable-ChocolateySource -All
+            Enable-ChocolateySource -Name 'hermes-all'
+
+            $Output = Invoke-Choco install $PackageName --confirm
+            $Packages = Get-ChocolateyInstalledPackages
+        }
+
+        It "Exits correctly (15608)" {
+            # failingdependency exits with 15608, so Chocolatey exits with that.
+            $Output.ExitCode | Should -Be 15608 -Because $Output.String
+        }
+
+        It "Should have the expected packages" {
+            $ExpectedPackages = @(
+                "downgradesdependency"
+                "hasnesteddependency"
+                "isdependency"
+                "hasdependency"
+            )
+            $UnexpectedPackages = @(
+                "dependencyfailure"
+                "isexactversiondependency"
+                'dependencyfailure'
+                'hasfailingnesteddependency'
+            )
+
+            foreach ($package in $ExpectedPackages) {
+                $Packages.Name | Should -Contain $package -Because "Package: $package $($Output.String)"
+            }
+
+            foreach ($package in $UnexpectedPackages) {
+                $Packages.Name | Should -Not -Contain $package -Because "Package: $package $($Output.String)"
+            }
+        }
+    }
+
     # This needs to be the last test in this block, to ensure NuGet configurations aren't being created.
     # Any tests after this block are expected to generate the configuration as they're explicitly using the NuGet CLI
     Test-NuGetPaths
diff --git a/tests/pester-tests/commands/choco-upgrade.Tests.ps1 b/tests/pester-tests/commands/choco-upgrade.Tests.ps1
index 460b72ec64..0eb1329ba4 100644
--- a/tests/pester-tests/commands/choco-upgrade.Tests.ps1
+++ b/tests/pester-tests/commands/choco-upgrade.Tests.ps1
@@ -736,6 +736,102 @@ To upgrade a local, or remote file, you may use:
         }
     }
 
+    Context 'Upgrading a package (<PackageName>) with <Argument> should downgrade (<AllowsDowngrade>) an existing package dependency.' -Tag Downgrade -ForEach @(
+        @{
+            Argument = '--force'
+            AllowsDowngrade = $true
+            ExpectedExit = 0
+            PackageName = 'upgradedowngradesdependency'
+            BasePackage = 'upgradedowngradesdependency'
+        }
+        @{
+            Argument = '--allow-downgrade'
+            AllowsDowngrade = $true
+            ExpectedExit = 0
+            PackageName = 'upgradedowngradesdependency'
+            BasePackage = 'upgradedowngradesdependency'
+        }
+        @{
+            Argument = ''
+            AllowsDowngrade = $false
+            ExpectedExit = 1
+            PackageName = 'upgradedowngradesdependency'
+            BasePackage = 'upgradedowngradesdependency'
+        }
+        @{
+            Argument = '--force'
+            AllowsDowngrade = $true
+            ExpectedExit = 0
+            PackageName = 'all'
+            BasePackage = 'upgradedowngradesdependency'
+        }
+        @{
+            Argument = '--allow-downgrade'
+            AllowsDowngrade = $true
+            ExpectedExit = 0
+            PackageName = 'all'
+            BasePackage = 'upgradedowngradesdependency'
+        }
+        @{
+            Argument = ''
+            AllowsDowngrade = $false
+            ExpectedExit = 1
+            PackageName = 'all'
+            BasePackage = 'upgradedowngradesdependency'
+        }
+        @{
+            Argument = '--force'
+            AllowsDowngrade = $true
+            ExpectedExit = 0
+            PackageName = 'all'
+            BasePackage = 'downgradesdependency'
+        }
+        @{
+            Argument = '--allow-downgrade'
+            AllowsDowngrade = $true
+            ExpectedExit = 0
+            PackageName = 'all'
+            BasePackage = 'downgradesdependency'
+        }
+        @{
+            Argument = ''
+            AllowsDowngrade = $false
+            ExpectedExit = 1
+            PackageName = 'all'
+            BasePackage = 'downgradesdependency'
+        }
+    ) {
+        BeforeAll {
+            $DependentPackage = @{
+                Name = 'isdependency'
+                Version = '2.1.0'
+            }
+
+            Restore-ChocolateyInstallSnapshot
+
+            $Setup = Invoke-Choco install $DependentPackage.Name --version $DependentPackage.Version --confirm
+            $Setup2 = Invoke-Choco install $BasePackage --version 1.0.0 --confirm
+            $Output = Invoke-Choco upgrade $PackageName --confirm --except="'chocolatey'" $Argument
+        }
+
+        It "Exits with expected result (<ExpectedExit>)" {
+            $Output.ExitCode | Should -Be $ExpectedExit -Because $Output.String
+        }
+
+        It "Reports correctly about downgrading isdependency" {
+            if ($AllowsDowngrade) {
+                $Output.Lines | Should -Not -Contain 'A newer version of isdependency (v2.1.0) is already installed.' -Because $Output.String
+                $Output.Lines | Should -Not -Contain 'Use --allow-downgrade or --force to attempt to install older versions.' -Because $Output.String
+                $Output.String | Should -MatchExactly 'Chocolatey upgraded 2/\d+ packages.'
+            }
+            else {
+                $Output.Lines | Should -Contain 'A newer version of isdependency (v2.1.0) is already installed.' -Because $Output.String
+                $Output.Lines | Should -Contain 'Use --allow-downgrade or --force to attempt to install older versions.' -Because $Output.String
+                $Output.String | Should -MatchExactly 'Chocolatey upgraded 0/\d+ packages. 2 packages failed.'
+            }
+        }
+    }
+
     # This needs to be (almost) the last test in this block, to ensure NuGet configurations aren't being created.
     # Any tests after this block are expected to generate the configuration as they're explicitly using the NuGet CLI
     Test-NuGetPaths
diff --git a/tests/pester-tests/commands/failingnested.packages.config b/tests/pester-tests/commands/failingnested.packages.config
new file mode 100644
index 0000000000..698f931c4f
--- /dev/null
+++ b/tests/pester-tests/commands/failingnested.packages.config
@@ -0,0 +1,11 @@
+<?xml version="1.0" encoding="utf-8"?>
+<packages>
+  <package id="dependencyfailure" />
+  <package id="downgradesdependency" />
+  <package id="failingdependency" />
+  <package id="hasdependency" />
+  <package id="hasfailingnesteddependency" />
+  <package id="hasnesteddependency" />
+  <package id="isdependency" />
+  <package id="isexactversiondependency" />
+</packages>