diff --git a/apps/desktop/src/shared/main/header-listen-button.tsx b/apps/desktop/src/shared/main/header-listen-button.tsx
index 644cf36f21..0d8c2b2af1 100644
--- a/apps/desktop/src/shared/main/header-listen-button.tsx
+++ b/apps/desktop/src/shared/main/header-listen-button.tsx
@@ -1,9 +1,16 @@
-import { ChevronDownIcon } from "lucide-react";
-import { useCallback, useState } from "react";
+import { ChevronDown } from "lucide-react";
+import {
+  type MouseEvent,
+  useCallback,
+  useEffect,
+  useRef,
+  useState,
+} from "react";
 
 import { Button } from "@hypr/ui/components/ui/button";
 import {
   Popover,
+  PopoverAnchor,
   PopoverContent,
   PopoverTrigger,
 } from "@hypr/ui/components/ui/popover";
@@ -84,15 +91,50 @@ function useHeaderListenState() {
 
 function HeaderListenButtonInner() {
   const { isDisabled, warningMessage } = useHeaderListenState();
+  const [menuWidth, setMenuWidth] = useState<number | null>(null);
+  const containerRef = useRef<HTMLDivElement | null>(null);
   const handleClick = useNewNoteAndListen();
   const handleUpload = useNewNoteAndUpload();
   const openNew = useTabs((state) => state.openNew);
   const [open, setOpen] = useState(false);
 
+  useEffect(() => {
+    const node = containerRef.current;
+
+    if (!node) {
+      return;
+    }
+
+    const updateWidth = () => {
+      setMenuWidth(node.offsetWidth);
+    };
+
+    updateWidth();
+
+    const observer = new ResizeObserver(updateWidth);
+    observer.observe(node);
+
+    return () => {
+      observer.disconnect();
+    };
+  }, []);
+
   const handleConfigure = useCallback(() => {
     openNew({ type: "ai", state: { tab: "transcription" } });
   }, [openNew]);
 
+  const handleMenuMouseDown = useCallback((event: MouseEvent) => {
+    if (event.button === 2) {
+      event.preventDefault();
+    }
+  }, []);
+
+  const handleOpenMenu = useCallback((event: MouseEvent) => {
+    event.preventDefault();
+    event.stopPropagation();
+    setOpen(true);
+  }, []);
+
   const handleUploadAudio = useCallback(() => {
     setOpen(false);
     handleUpload("audio").catch((error) => {
@@ -111,15 +153,17 @@ function HeaderListenButtonInner() {
     <button
       type="button"
       onClick={handleClick}
+      onMouseDown={handleMenuMouseDown}
+      onContextMenu={handleOpenMenu}
       disabled={isDisabled}
       className={cn([
-        "inline-flex items-center justify-center rounded-full text-sm font-medium text-white",
+        "inline-flex items-center justify-center rounded-full text-sm font-medium text-white select-none",
         "gap-2",
         "h-8 pr-8 pl-4",
         "border-2 border-stone-600 bg-stone-800",
         "transition-all duration-200 ease-out",
         "hover:bg-stone-700",
-        "disabled:pointer-events-none disabled:opacity-50",
+        "disabled:opacity-50",
       ])}
     >
       <RecordingIcon />
@@ -130,54 +174,68 @@ function HeaderListenButtonInner() {
   const chevron = (
     <button
       type="button"
-      className="absolute top-1/2 right-1.5 z-10 -translate-y-1/2 cursor-pointer text-white/70 transition-colors hover:text-white"
-      onClick={(e) => {
-        e.stopPropagation();
+      className="absolute inset-y-0 right-0 z-10 inline-flex w-9 cursor-pointer items-center justify-center rounded-r-full bg-transparent text-white/70 transition-colors select-none hover:text-white"
+      onMouseDown={handleMenuMouseDown}
+      onClick={(event) => {
+        event.stopPropagation();
       }}
     >
-      <ChevronDownIcon className="size-3.5" />
+      <ChevronDown className="size-3.5" />
       <span className="sr-only">More options</span>
     </button>
   );
 
-  const content = (
+  return (
     <Popover open={open} onOpenChange={setOpen}>
-      <div className="relative flex items-center">
-        {warningMessage ? (
-          <Tooltip delayDuration={0}>
-            <TooltipTrigger asChild>{button}</TooltipTrigger>
-            <TooltipContent side="bottom">
-              <ActionableTooltipContent
-                message={warningMessage}
-                action={{
-                  label: "Configure",
-                  handleClick: handleConfigure,
-                }}
-              />
-            </TooltipContent>
-          </Tooltip>
-        ) : (
-          button
-        )}
-        <PopoverTrigger asChild>{chevron}</PopoverTrigger>
-      </div>
+      <PopoverAnchor asChild>
+        <div
+          ref={containerRef}
+          className="relative flex items-center select-none"
+          onMouseDownCapture={handleMenuMouseDown}
+          onContextMenu={handleOpenMenu}
+        >
+          {warningMessage ? (
+            <Tooltip delayDuration={0}>
+              <TooltipTrigger asChild>
+                <span className="inline-flex">{button}</span>
+              </TooltipTrigger>
+              <TooltipContent side="bottom">
+                <ActionableTooltipContent
+                  message={warningMessage}
+                  action={{
+                    label: "Configure",
+                    handleClick: handleConfigure,
+                  }}
+                />
+              </TooltipContent>
+            </Tooltip>
+          ) : (
+            button
+          )}
+          <PopoverTrigger asChild>{chevron}</PopoverTrigger>
+        </div>
+      </PopoverAnchor>
       <PopoverContent
         side="bottom"
         align="end"
         sideOffset={4}
-        className="w-43 rounded-xl p-1.5"
+        style={menuWidth ? { width: menuWidth } : undefined}
+        className={cn([
+          "overflow-hidden rounded-[1.25rem] border border-white/70 p-1.5 ring-1 ring-black/6 outline-none",
+          "bg-white/68 text-stone-900 shadow-[inset_0_1px_0_rgba(255,255,255,0.7),0_24px_48px_-24px_rgba(48,44,40,0.52),0_8px_18px_rgba(255,255,255,0.28)] backdrop-blur-md backdrop-saturate-150",
+        ])}
       >
         <div className="flex flex-col gap-1">
           <Button
             variant="ghost"
-            className="h-9 justify-center px-3 whitespace-nowrap"
+            className="h-9 w-full justify-center rounded-[0.95rem] px-3 text-sm text-stone-900 shadow-none hover:bg-black/6 hover:text-stone-950 focus-visible:ring-0 focus-visible:outline-none"
             onClick={handleUploadAudio}
           >
             <span className="text-sm">Upload audio</span>
           </Button>
           <Button
             variant="ghost"
-            className="h-9 justify-center px-3 whitespace-nowrap"
+            className="h-9 w-full justify-center rounded-[0.95rem] px-3 text-sm text-stone-900 shadow-none hover:bg-black/6 hover:text-stone-950 focus-visible:ring-0 focus-visible:outline-none"
             onClick={handleUploadTranscript}
           >
             <span className="text-sm">Upload transcript</span>
@@ -186,6 +244,4 @@ function HeaderListenButtonInner() {
       </PopoverContent>
     </Popover>
   );
-
-  return content;
 }