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I have an application pinned to the task bar. 90% of the time, I run it with no additional command line options, so I can either click it (if not already open), or right click the icon and click the application name to open a new instance.

I want to make it where when I right click it, there are 2 options listed: the first is the program with no command line options and the second is the one with a custom command line (that I hard code). If this is impossible, it would be tolerable to add it to the extended context menu (shift + right click the icon), but I prefer the former.

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I think you mean adding entries into what are called the Jump List (basically the menu that pops up when you right click an icon). I don't know if there is a way to edit things you pin to the bar but I did see this application that lets you define custom lists.

JumpList Launcher

You could use this to make a two entry list, one for each of the options you need.

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So you've already got an icon pinned to your task bar?

If that's the case, all you need to do is create a shortcut (using Windows Explorer) which includes the command line options you want. Run the shortcut to make sure it's right, then drag and drop it onto the icon pinned to your task bar. Then you'll have two items in your jump list.

Matthew

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You could try 7stacks. It would let you pin a shortcut to the menu that would contain the two versions of your shortcut. That means the primary one is always two clicks away and I notice a slight delay before it's menu shows up.

Since I found it less than intuitive...

  • Run it after install and you get the "create a new 7stack" dialog
  • Point it at a folder that contains your two shortcuts
  • Give it a Caption (and Icon if desired)
  • Click the "Create a Shortcut on Desktop" button
  • Find that Shortcut on your Desktop (the name is the Caption you set earlier)
  • Right-click the shortcut and "Pin to Taskbar"

You can right-click to edit it or create new ones.

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