diff --git a/src/chocolatey.resources/helpers/ChocolateyTabExpansion.ps1 b/src/chocolatey.resources/helpers/ChocolateyTabExpansion.ps1
index 9e32783f06..5d4209a3b5 100644
--- a/src/chocolatey.resources/helpers/ChocolateyTabExpansion.ps1
+++ b/src/chocolatey.resources/helpers/ChocolateyTabExpansion.ps1
@@ -38,7 +38,7 @@ function script:chocoCmdOperations($commands, $command, $filter, $currentArgumen
 $script:chocoCommands = @('-?','search','list','info','install','outdated','upgrade','uninstall','new','pack','push','-h','--help','pin','source','config','feature','apikey','export','help','template','--version')
 
 # ensure these all have a space to start, or they will cause issues
-$allcommands = " --debug --verbose --trace --noop --help -? --accept-license --confirm --limit-output --no-progress --log-file='' --execution-timeout='' --cache-location='' --proxy='' --proxy-user='' --proxy-password='' --proxy-bypass-list='' --proxy-bypass-on-local --force --no-color --skip-compatibility-checks"
+$allcommands = " --debug --verbose --trace --noop --help -? --online --accept-license --confirm --limit-output --no-progress --log-file='' --execution-timeout='' --cache-location='' --proxy='' --proxy-user='' --proxy-password='' --proxy-bypass-list='' --proxy-bypass-on-local --force --no-color --skip-compatibility-checks"
 
 $commandOptions = @{
     list      = "--id-only --pre --exact --by-id-only --id-starts-with --detailed --prerelease --include-programs --page='' --page-size=''"
diff --git a/src/chocolatey.tests.integration/Scenario.cs b/src/chocolatey.tests.integration/Scenario.cs
index d417e2de7f..53a17c11ce 100644
--- a/src/chocolatey.tests.integration/Scenario.cs
+++ b/src/chocolatey.tests.integration/Scenario.cs
@@ -285,6 +285,7 @@ private static ChocolateyConfiguration baseline_configuration()
             config.ForceDependencies = false;
             config.ForceX86 = false;
             config.HelpRequested = false;
+            config.ShowOnlineHelp = false;
             config.UnsuccessfulParsing = false;
             config.UnsuccessfulParsing = false;
             config.IgnoreDependencies = false;
diff --git a/src/chocolatey.tests/infrastructure.app/configuration/ConfigurationOptionsSpec.cs b/src/chocolatey.tests/infrastructure.app/configuration/ConfigurationOptionsSpec.cs
index a07fdd7e6a..f076c05c5a 100644
--- a/src/chocolatey.tests/infrastructure.app/configuration/ConfigurationOptionsSpec.cs
+++ b/src/chocolatey.tests/infrastructure.app/configuration/ConfigurationOptionsSpec.cs
@@ -100,6 +100,19 @@ public void Should_show_help_menu_when_help_is_requested()
                 because();
 
                 config.HelpRequested.ShouldBeTrue();
+                config.ShowOnlineHelp.ShouldBeFalse();
+            }
+
+            [Fact]
+            public void Should_show_online_help_menu_when_help_is_requested()
+            {
+                args.Add("-h");
+                args.Add("--online");
+
+                because();
+
+                config.HelpRequested.ShouldBeTrue();
+                config.ShowOnlineHelp.ShouldBeTrue();
             }
 
             [Fact]
diff --git a/src/chocolatey/infrastructure.app/builders/ConfigurationBuilder.cs b/src/chocolatey/infrastructure.app/builders/ConfigurationBuilder.cs
index 3e90eed2fc..67cc2b401f 100644
--- a/src/chocolatey/infrastructure.app/builders/ConfigurationBuilder.cs
+++ b/src/chocolatey/infrastructure.app/builders/ConfigurationBuilder.cs
@@ -448,8 +448,11 @@ private static void SetGlobalOptions(IList<string> args, ChocolateyConfiguration
                 {
                     if (!string.IsNullOrWhiteSpace(config.CommandName))
                     {
-                        // save help for next menu
+                        // The setOptions lambda above is called twice, once to set the command name, and then to execute the command with all options.
+                        // To ensure correct option of the help options, we need to reset them to false in the first execution, to then have them parsed correctly in the second
+                        // iteration.
                         config.HelpRequested = false;
+                        config.ShowOnlineHelp = false;
                         config.UnsuccessfulParsing = false;
                     }
                 },
diff --git a/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs b/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
index 8093447e92..19955e5558 100644
--- a/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
+++ b/src/chocolatey/infrastructure.app/configuration/ChocolateyConfiguration.cs
@@ -263,6 +263,7 @@ private void AppendOutput(StringBuilder propertyValues, string append)
 
         // top level commands
 
+        public bool ShowOnlineHelp { get; set; }
         public bool Debug { get; set; }
         public bool Verbose { get; set; }
         public bool Trace { get; set; }
diff --git a/src/chocolatey/infrastructure.app/configuration/ConfigurationOptions.cs b/src/chocolatey/infrastructure.app/configuration/ConfigurationOptions.cs
index 6935c3c377..8a19f00c1e 100644
--- a/src/chocolatey/infrastructure.app/configuration/ConfigurationOptions.cs
+++ b/src/chocolatey/infrastructure.app/configuration/ConfigurationOptions.cs
@@ -19,6 +19,7 @@ namespace chocolatey.infrastructure.app.configuration
     using System;
     using System.Collections.Generic;
     using System.ComponentModel;
+    using System.Diagnostics;
     using System.Linq;
     using System.Text.RegularExpressions;
     using adapters;
@@ -75,8 +76,11 @@ public static void ParseArgumentsAndUpdateConfiguration(ICollection<string> args
             {
                 _optionSet
                     .Add("?|help|h",
-                         "Prints out the help menu.",
-                         option => configuration.HelpRequested = option != null);
+                        "Prints out the help menu.",
+                        option => configuration.HelpRequested = option != null)
+                    .Add("online",
+                        "Online - Open help for specified command in default browser application. This option only works when used in combintation with the -?/--help/-h option.",
+                        option => configuration.ShowOnlineHelp = option != null);
             }
 
             if (setOptions != null)
@@ -120,10 +124,38 @@ public static void ParseArgumentsAndUpdateConfiguration(ICollection<string> args
 
             if (configuration.HelpRequested)
             {
+                if (configuration.ShowOnlineHelp)
+                {
+                    if (string.IsNullOrWhiteSpace(configuration.CommandName))
+                    {
+                        "chocolatey".Log().Warn("Unable to open command help as no command name has been provided.");
+                        return;
+                    }
+
+                    var targetAddress = "https://ch0.co/c/{0}".FormatWith(configuration.CommandName.ToLowerSafe());
+
+                    try
+                    {
+                        System.Diagnostics.Process.Start(new ProcessStartInfo(targetAddress) { UseShellExecute = true });
+                    }
+                    catch (Exception)
+                    {
+                        "chocolatey".Log().Warn("There was an error while attempting to open the following URL: {0} in the default browser.".FormatWith(targetAddress));
+                    }
+
+                    return;
+                }
+
                 ShowHelp(_optionSet, helpMessage);
             }
             else
             {
+                // Only show this warning once
+                if (configuration.ShowOnlineHelp)
+                {
+                    "chocolatey".Log().Warn("The --online option has been used, without the corresponding -?/--help/-h option.  Command execution will be completed without invoking help.");
+                }
+
                 if (validateConfiguration != null)
                 {
                     validateConfiguration();