diff --git a/src/chocolatey/infrastructure.app/commands/ChocolateyUpgradeCommand.cs b/src/chocolatey/infrastructure.app/commands/ChocolateyUpgradeCommand.cs
index 8c8080d3b8..e0294c2b46 100644
--- a/src/chocolatey/infrastructure.app/commands/ChocolateyUpgradeCommand.cs
+++ b/src/chocolatey/infrastructure.app/commands/ChocolateyUpgradeCommand.cs
@@ -235,6 +235,10 @@ public virtual void ConfigureArgumentParser(OptionSet optionSet, ChocolateyConfi
                     "Skip hooks - Do not run hook scripts. Available in 1.2.0+",
                     option => configuration.SkipHookScripts = option != null
                     )
+                .Add("bypass-pins|ignore-pins",
+                    "Bypass Pin(s) - Bypass any pins and upgrade the packages anyways. Defaults to false. Available in 2.2.0+",
+                    option => configuration.UpgradeCommand.BypassPins = option != null
+                    )
                 ;
         }
 
diff --git a/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs b/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
index 5ec4816f43..6c974f1d96 100644
--- a/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
+++ b/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
@@ -600,6 +600,7 @@ 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 354fa6ca6e..b1bba6f8b4 100644
--- a/src/chocolatey/infrastructure.app/services/NugetService.cs
+++ b/src/chocolatey/infrastructure.app/services/NugetService.cs
@@ -1045,7 +1045,7 @@ public virtual ConcurrentDictionary<string, PackageResult> Upgrade(ChocolateyCon
                 var pkgInfo = _packageInfoService.Get(installedPackage.PackageMetadata);
                 bool isPinned = pkgInfo != null && pkgInfo.IsPinned;
 
-                if (isPinned && config.OutdatedCommand.IgnorePinned)
+                if (isPinned && config.OutdatedCommand.IgnorePinned && !config.UpgradeCommand.BypassPins)
                 {
                     continue;
                 }
@@ -1174,12 +1174,21 @@ public virtual ConcurrentDictionary<string, PackageResult> Upgrade(ChocolateyCon
 
                     if (isPinned)
                     {
-                        string logMessage = "{0} is pinned. Skipping pinned package.".FormatWith(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;
+                        if (!config.UpgradeCommand.BypassPins)
+                        {
+                            string logMessage = "{0} is pinned. Skipping pinned package.".FormatWith(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;
+                        }
+                        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;
+                        }
                     }
 
                     if (performAction)