diff --git a/.server-changes/fix-sidebar-feedback.md b/.server-changes/fix-sidebar-feedback.md
new file mode 100644
index 00000000000..066332c0314
--- /dev/null
+++ b/.server-changes/fix-sidebar-feedback.md
@@ -0,0 +1,6 @@
+---
+area: webapp
+type: fix
+---
+
+Fix the sidebar "Help & Feedback → Contact us" form sometimes not sending your message. It now sends reliably every time.
diff --git a/apps/webapp/app/components/Feedback.tsx b/apps/webapp/app/components/Feedback.tsx
index ebd61180de5..b679b042da1 100644
--- a/apps/webapp/app/components/Feedback.tsx
+++ b/apps/webapp/app/components/Feedback.tsx
@@ -9,7 +9,7 @@ import { parseWithZod } from "@conform-to/zod";
 import { InformationCircleIcon, ArrowUpCircleIcon } from "@heroicons/react/20/solid";
 import { EnvelopeIcon, ShieldCheckIcon } from "@heroicons/react/24/solid";
 import { Form, useActionData, useLocation, useNavigation, useSearchParams } from "@remix-run/react";
-import { type ReactNode, useEffect, useState } from "react";
+import { type ReactNode, useEffect, useRef, useState } from "react";
 import { type FeedbackType, feedbackTypes, schema } from "~/routes/resources.feedback";
 import { Button } from "./primitives/Buttons";
 import { Dialog, DialogContent, DialogHeader, DialogTrigger } from "./primitives/Dialog";
@@ -27,13 +27,26 @@ import { TextLink } from "./primitives/TextLink";
 import { DialogClose } from "@radix-ui/react-dialog";
 
 type FeedbackProps = {
-  button: ReactNode;
+  button?: ReactNode;
   defaultValue?: FeedbackType;
   onOpenChange?: (open: boolean) => void;
-};
+} &
+  // Controlled mode is all-or-none: pass both open + setOpen to host the dialog outside a popover
+  // (so the popover closing can't unmount the form mid-submit and cancel the feedback POST), or
+  // neither for the self-managed, button-triggered dialog. Passing only one is a broken half-state.
+  ({ open?: never; setOpen?: never } | { open: boolean; setOpen: (open: boolean) => void });
 
-export function Feedback({ button, defaultValue = "bug", onOpenChange }: FeedbackProps) {
-  const [open, setOpen] = useState(false);
+export function Feedback({
+  button,
+  defaultValue = "bug",
+  onOpenChange,
+  open: openProp,
+  setOpen: setOpenProp,
+}: FeedbackProps) {
+  const [openState, setOpenState] = useState(false);
+  // Controlled when the caller passes open/setOpen (hosted outside a popover); otherwise self-managed.
+  const open = openProp ?? openState;
+  const setOpen = setOpenProp ?? setOpenState;
   const [searchParams, setSearchParams] = useSearchParams();
   const location = useLocation();
   const lastSubmission = useActionData();
@@ -72,6 +85,18 @@ export function Feedback({ button, defaultValue = "bug", onOpenChange }: Feedbac
     }
   }, [searchParams]);
 
+  // Reset the topic to the default once the dialog closes, so reopening always starts fresh. The
+  // dialog is now persistently mounted (hosted outside the popover), so without this it would keep
+  // the previously chosen topic selected and risk filing feedback under the wrong category. Keyed
+  // on the close transition (not just `!open`) so the ?feedbackPanel= open path isn't clobbered.
+  const wasOpen = useRef(open);
+  useEffect(() => {
+    if (wasOpen.current && !open) {
+      setType(defaultValue);
+    }
+    wasOpen.current = open;
+  }, [open, defaultValue]);
+
   const handleOpenChange = (value: boolean) => {
     setOpen(value);
     onOpenChange?.(value);
@@ -79,7 +104,7 @@ export function Feedback({ button, defaultValue = "bug", onOpenChange }: Feedbac
 
   return (
     <Dialog open={open} onOpenChange={handleOpenChange}>
-      <DialogTrigger asChild>{button}</DialogTrigger>
+      {button ? <DialogTrigger asChild>{button}</DialogTrigger> : null}
       <DialogContent>
         <DialogHeader>Contact us</DialogHeader>
         <div className="mt-2 flex flex-col gap-4">
diff --git a/apps/webapp/app/components/navigation/HelpAndFeedbackPopover.tsx b/apps/webapp/app/components/navigation/HelpAndFeedbackPopover.tsx
index 669271fe766..c7276dd5bc6 100644
--- a/apps/webapp/app/components/navigation/HelpAndFeedbackPopover.tsx
+++ b/apps/webapp/app/components/navigation/HelpAndFeedbackPopover.tsx
@@ -35,6 +35,10 @@ export function HelpAndFeedback({
   projectId?: string;
 }) {
   const [isHelpMenuOpen, setHelpMenuOpen] = useState(false);
+  // Hosted outside the popover (below) and opened from the menu item, so the popover closing never
+  // unmounts the feedback form mid-submit — that teardown was intermittently canceling the POST to
+  // /resources/feedback, so messages sent from the sidebar were silently lost.
+  const [isFeedbackOpen, setFeedbackOpen] = useState(false);
   const _currentPlan = useCurrentPlan();
   const { changelogs } = useRecentChangelogs(organizationId, projectId);
 
@@ -164,14 +168,14 @@ export function HelpAndFeedback({
                     target="_blank"
                   />
                   <Shortcuts />
-                  <Feedback
-                    button={
-                      <SideMenuItemButton
-                        icon={EnvelopeIcon}
-                        name="Contact us…"
-                        data-action="contact-us"
-                      />
-                    }
+                  <SideMenuItemButton
+                    icon={EnvelopeIcon}
+                    name="Contact us…"
+                    data-action="contact-us"
+                    onClick={() => {
+                      setHelpMenuOpen(false);
+                      setFeedbackOpen(true);
+                    }}
                   />
                 </div>
                 <div className="flex flex-col gap-1 p-1">
@@ -206,6 +210,8 @@ export function HelpAndFeedback({
           </Popover>
         )}
       </AskAIRoot>
+      {/* Hosted outside the popover so closing the menu can't unmount the form mid-submit. */}
+      <Feedback open={isFeedbackOpen} setOpen={setFeedbackOpen} />
     </motion.div>
   );
 }