diff --git a/aegisub/src/command/command.h b/aegisub/src/command/command.h
index db9d4dd36..008fe805a 100644
--- a/aegisub/src/command/command.h
+++ b/aegisub/src/command/command.h
@@ -79,8 +79,11 @@ namespace cmd {
 		/// This command's name may change based on the state of the project
 		COMMAND_DYNAMIC_NAME = 8,
 
+		/// This command's help string may change
+		COMMAND_DYNAMIC_HELP = 16,
+
 		/// This command's icon may change based on the state of the project
-		COMMAND_DYNAMIC_ICON = 16
+		COMMAND_DYNAMIC_ICON = 32
 	};
 
 	/// Holds an individual Command
@@ -93,7 +96,7 @@ namespace cmd {
 		/// Plain string for display purposes; should normally be the same as StrMenu
 		/// but without accelerators
 		virtual wxString StrDisplay(const agi::Context *) const=0;
-		/// Short help string descripting the command purpose.
+		/// Short help string describing what the command does
 		virtual wxString StrHelp() const=0;
 
 		/// Get this command's type flags
diff --git a/aegisub/src/menu.cpp b/aegisub/src/menu.cpp
index 646d0de38..914d88e6b 100644
--- a/aegisub/src/menu.cpp
+++ b/aegisub/src/menu.cpp
@@ -148,6 +148,8 @@ class CommandManager {
 		int flags = c->Type();
 		if (flags & cmd::COMMAND_DYNAMIC_NAME)
 			UpdateItemName(item);
+		if (flags & cmd::COMMAND_DYNAMIC_HELP)
+			item.second->SetHelp(c->StrHelp());
 		if (flags & cmd::COMMAND_VALIDATE)
 			item.second->Enable(c->Validate(context));
 		if (flags & cmd::COMMAND_RADIO || flags & cmd::COMMAND_TOGGLE) {