diff --git a/src/chocolatey/infrastructure.app/commands/ChocolateyUpgradeCommand.cs b/src/chocolatey/infrastructure.app/commands/ChocolateyUpgradeCommand.cs
index a45ca6e615..0caa6aa2bf 100644
--- a/src/chocolatey/infrastructure.app/commands/ChocolateyUpgradeCommand.cs
+++ b/src/chocolatey/infrastructure.app/commands/ChocolateyUpgradeCommand.cs
@@ -165,7 +165,7 @@ public virtual void configure_argument_parser(OptionSet optionSet, ChocolateyCon
                 .Add("stoponfirstfailure|stop-on-first-failure|stop-on-first-package-failure",
                      "Stop On First Package Failure - stop running install, upgrade or uninstall on first package failure instead of continuing with others. Overrides the default feature '{0}' set to '{1}'. Available in 0.10.4+.".format_with(ApplicationParameters.Features.StopOnFirstPackageFailure, configuration.Features.StopOnFirstPackageFailure.to_string()),
                      option => configuration.Features.StopOnFirstPackageFailure = option != null
-                     ) 
+                     )
                 .Add("skip-if-not-installed|only-upgrade-installed|skip-when-not-installed",
                      "Skip Packages Not Installed - if a package is not installed, do not install it during the upgrade process. Overrides the default feature '{0}' set to '{1}'. Available in 0.10.12+.".format_with(ApplicationParameters.Features.SkipPackageUpgradesWhenNotInstalled, configuration.Features.SkipPackageUpgradesWhenNotInstalled.to_string()),
                      option => configuration.Features.SkipPackageUpgradesWhenNotInstalled = option != null
@@ -224,6 +224,9 @@ public virtual void configure_argument_parser(OptionSet optionSet, ChocolateyCon
                     "Pin Package - Add a pin to the package after upgrade. Available in 0.11.12+",
                     option => configuration.PinPackage = option != null
                     )
+                .Add("bypass-pins|ignore-pins",
+                    "Bypass Pin(s) - Bypass any pins and upgrade the packages anyways. Defaults to false. Available in 1.0.0+",
+                    option => configuration.UpgradeCommand.BypassPins = option != null)
                 ;
         }
 
@@ -307,7 +310,7 @@ choco upgrade notepadplusplus googlechrome atom 7zip -dvfy
     choco upgrade git -y --params=""'/GitAndUnixToolsOnPath /NoAutoCrlf'""
     choco upgrade git -y --params=""'/GitAndUnixToolsOnPath /NoAutoCrlf'"" --install-args=""'/DIR=C:\git'""
     # Params are package parameters, passed to the package
-    # Install args are installer arguments, appended to the silentArgs 
+    # Install args are installer arguments, appended to the silentArgs
     #  in the package for the installer itself
     choco upgrade nodejs.install --version 0.10.35
     choco upgrade git -s ""'https://somewhere/out/there'""
@@ -315,7 +318,7 @@ choco upgrade nodejs.install --version 0.10.35
     choco upgrade all
     choco upgrade all --except=""'skype,conemu'""
 
-NOTE: See scripting in the command reference (`choco -?`) for how to 
+NOTE: See scripting in the command reference (`choco -?`) for how to
  write proper scripts and integrations.
 
 ");
@@ -347,7 +350,7 @@ when the feature '{1}' is turned on. It typically requires
  the feature '{0}' to also be turned on to work properly.
  Available in v0.10.12+.
 ".format_with(ApplicationParameters.Features.UsePackageExitCodes, ApplicationParameters.Features.ExitOnRebootDetected));
-            
+
             "chocolatey".Log().Info(ChocolateyLoggers.Important, "See It In Action");
             "chocolatey".Log().Info(@"
 choco upgrade: https://raw.githubusercontent.com/wiki/chocolatey/choco/images/gifs/choco_upgrade.gif
diff --git a/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs b/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
index 97cabfc2ca..8de2786e0d 100644
--- a/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
+++ b/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
@@ -450,6 +450,7 @@ public sealed class UpgradeCommandConfiguration
         public bool NotifyOnlyAvailableUpgrades { get; set; }
         public string PackageNamesToSkip { get; set; }
         public bool ExcludePrerelease { get; set; }
+        public bool BypassPins { get; set; }
     }
 
     [Serializable]
diff --git a/src/chocolatey/infrastructure.app/services/NugetService.cs b/src/chocolatey/infrastructure.app/services/NugetService.cs
index ca285817bb..3d426d94f4 100644
--- a/src/chocolatey/infrastructure.app/services/NugetService.cs
+++ b/src/chocolatey/infrastructure.app/services/NugetService.cs
@@ -680,7 +680,7 @@ public virtual ConcurrentDictionary<string, PackageResult> upgrade_run(Chocolate
                 var pkgInfo = _packageInfoService.get_package_information(installedPackage);
                 bool isPinned = pkgInfo != null && pkgInfo.IsPinned;
 
-                if (isPinned && config.OutdatedCommand.IgnorePinned)
+                if (isPinned && config.OutdatedCommand.IgnorePinned && !config.UpgradeCommand.BypassPins)
                 {
                     continue;
                 }
@@ -812,12 +812,25 @@ public virtual ConcurrentDictionary<string, PackageResult> upgrade_run(Chocolate
 
                     if (isPinned)
                     {
-                        string logMessage = "{0} is pinned. Skipping pinned package.".format_with(packageName);
-                        packageResult.Messages.Add(new ResultMessage(ResultType.Warn, logMessage));
-                        packageResult.Messages.Add(new ResultMessage(ResultType.Inconclusive, logMessage));
-                        if (config.RegularOutput) this.Log().Warn(ChocolateyLoggers.Important, logMessage);
+                        if (!config.UpgradeCommand.BypassPins)
+                        {
+                            string logMessage = "{0} is pinned. Skipping pinned package.".format_with(packageName);
+                            packageResult.Messages.Add(new ResultMessage(ResultType.Warn, logMessage));
+                            packageResult.Messages.Add(new ResultMessage(ResultType.Inconclusive, logMessage));
+                            if (config.RegularOutput) this.Log().Warn(ChocolateyLoggers.Important, logMessage);
 
-                        continue;
+                            continue;
+                        }
+                        else
+                        {
+                            string logMessage = "{0} is pinned. Upgrading pinned package anyway as bypass-pins is specified".format_with(packageName);
+                            packageResult.Messages.Add(new ResultMessage(ResultType.Warn, logMessage));
+                            if (config.RegularOutput) this.Log().Warn(ChocolateyLoggers.Important, logMessage);
+                            config.PinPackage = true;
+
+                            //Reset the config in ChocolateyPackageService in so the package will be re-pinned after install
+                            resetConfigAction(config);
+                        }
                     }
 
                     set_package_config_for_upgrade(config, pkgInfo);