diff --git a/modules/darwin/karabiner.nix b/modules/darwin/karabiner.nix
index 53f2112..d42182c 100644
--- a/modules/darwin/karabiner.nix
+++ b/modules/darwin/karabiner.nix
@@ -134,8 +134,35 @@ let
     name = "Complex Modifications";
     rules = [
       {
-        description = "Logitech mouse Button3 sends Fn, or middle click with Hyper or Button2";
+        description = "Logitech mouse Button3 sends Fn, or middle click with Hyper, Shift, Button1, or Button2";
         manipulators = [
+          {
+            from.pointing_button = "button1";
+            to = [
+              { pointing_button = "button1"; }
+              {
+                set_variable = {
+                  name = "logitech_mouse_button1_held";
+                  value = 1;
+                };
+              }
+            ];
+            to_after_key_up = [
+              {
+                set_variable = {
+                  name = "logitech_mouse_button1_held";
+                  value = 0;
+                };
+              }
+            ];
+            conditions = [
+              {
+                type = "device_if";
+                identifiers = [ logitechMouseIdentifiers ];
+              }
+            ];
+            type = "basic";
+          }
           {
             from.pointing_button = "button2";
             to = [
@@ -163,6 +190,25 @@ let
             ];
             type = "basic";
           }
+          {
+            from = {
+              pointing_button = "button3";
+              modifiers.optional = [ "any" ];
+            };
+            to = [ { pointing_button = "button3"; } ];
+            conditions = [
+              {
+                type = "device_if";
+                identifiers = [ logitechMouseIdentifiers ];
+              }
+              {
+                type = "variable_if";
+                name = "logitech_mouse_button1_held";
+                value = 1;
+              }
+            ];
+            type = "basic";
+          }
           {
             from = {
               pointing_button = "button3";
@@ -177,6 +223,23 @@ let
             ];
             type = "basic";
           }
+          {
+            from = {
+              pointing_button = "button3";
+              modifiers = {
+                mandatory = [ "shift" ];
+                optional = [ "any" ];
+              };
+            };
+            to = [ { pointing_button = "button3"; } ];
+            conditions = [
+              {
+                type = "device_if";
+                identifiers = [ logitechMouseIdentifiers ];
+              }
+            ];
+            type = "basic";
+          }
           {
             from = {
               pointing_button = "button3";