diff --git a/.server-changes/esc-to-close-fixes.md b/.server-changes/esc-to-close-fixes.md
new file mode 100644
index 00000000000..70e464ba106
--- /dev/null
+++ b/.server-changes/esc-to-close-fixes.md
@@ -0,0 +1,6 @@
+---
+area: webapp
+type: fix
+---
+
+Esc now closes the authenticator app setup window and the chat panel, and side sheets now show a close button with their Esc shortcut. Esc in the chat panel's message box just leaves the box, so an unsent message survives and a second Esc closes the panel. Closing a dialog with Esc no longer also closes the panel behind it, and the Vercel setup modal no longer shows a close button that does nothing.
diff --git a/apps/webapp/app/components/dashboard-agent/DashboardAgentComposer.tsx b/apps/webapp/app/components/dashboard-agent/DashboardAgentComposer.tsx
index 308a87ebab1..32f56c11a27 100644
--- a/apps/webapp/app/components/dashboard-agent/DashboardAgentComposer.tsx
+++ b/apps/webapp/app/components/dashboard-agent/DashboardAgentComposer.tsx
@@ -31,6 +31,11 @@ export function DashboardAgentComposer({
                 e.preventDefault();
                 onSubmit();
               }
+              // Esc leaves the composer, so a second Esc closes the panel and an
+              // unsent message survives the first one.
+              if (e.key === "Escape") {
+                e.currentTarget.blur();
+              }
             }}
             placeholder="Type a message…"
             className={cn(
diff --git a/apps/webapp/app/components/dashboard-agent/DashboardAgentHeader.tsx b/apps/webapp/app/components/dashboard-agent/DashboardAgentHeader.tsx
index 11d486bc1d3..fb125aedd7a 100644
--- a/apps/webapp/app/components/dashboard-agent/DashboardAgentHeader.tsx
+++ b/apps/webapp/app/components/dashboard-agent/DashboardAgentHeader.tsx
@@ -1,4 +1,5 @@
 import { ClockIcon, PencilSquareIcon, XMarkIcon } from "@heroicons/react/20/solid";
+import { Button } from "~/components/primitives/Buttons";
 import { cn } from "~/utils/cn";
 
 export function DashboardAgentHeader({
@@ -23,7 +24,15 @@ export function DashboardAgentHeader({
           onClick={onToggleHistory}
           active={view === "history"}
         />
-        <IconButton label="Close" icon={XMarkIcon} onClick={onClose} />
+        <Button
+          onClick={onClose}
+          variant="minimal/small"
+          TrailingIcon={XMarkIcon}
+          shortcut={{ key: "esc" }}
+          shortcutPosition="before-trailing-icon"
+          className="pl-1"
+          aria-label="Close"
+        />
       </div>
     </div>
   );
diff --git a/apps/webapp/app/components/errors/ConfigureErrorAlerts.tsx b/apps/webapp/app/components/errors/ConfigureErrorAlerts.tsx
index b126e77b34b..1b4c370ca83 100644
--- a/apps/webapp/app/components/errors/ConfigureErrorAlerts.tsx
+++ b/apps/webapp/app/components/errors/ConfigureErrorAlerts.tsx
@@ -7,7 +7,6 @@ import { useFetcher, useNavigate } from "@remix-run/react";
 import { SlackIcon } from "@trigger.dev/companyicons";
 import { Fragment, useEffect, useRef, useState } from "react";
 import { z } from "zod";
-import { ExitIcon } from "~/assets/icons/ExitIcon";
 import { InlineCode } from "~/components/code/InlineCode";
 import { Button, LinkButton } from "~/components/primitives/Buttons";
 import { Callout, variantClasses } from "~/components/primitives/Callout";
@@ -116,18 +115,10 @@ export function ConfigureErrorAlerts({
 
   return (
     <div className="grid h-full grid-rows-[auto_1fr_auto] overflow-hidden">
-      <div className="flex items-center justify-between border-b border-grid-bright px-3 py-2">
+      <div className="flex items-center border-b border-grid-bright py-2 pl-3 pr-16">
         <Header2 className="flex items-center gap-2">
           <BellAlertIcon className="size-5 text-alerts" /> Configure alerts
         </Header2>
-        <LinkButton
-          to={closeHref}
-          variant="minimal/small"
-          TrailingIcon={ExitIcon}
-          shortcut={{ key: "esc" }}
-          shortcutPosition="before-trailing-icon"
-          className="pl-1"
-        />
       </div>
 
       <fetcher.Form method="post" action={formAction} {...getFormProps(form)} className="contents">
diff --git a/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx b/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
index bda62a1b32f..530304391e0 100644
--- a/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
+++ b/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
@@ -747,7 +747,11 @@ export function VercelOnboardingModal({
           }
         }}
       >
-        <DialogContent className="max-w-lg" onInteractOutside={(e) => e.preventDefault()}>
+        <DialogContent
+          className="max-w-lg"
+          onInteractOutside={(e) => e.preventDefault()}
+          showCloseButton={!fromMarketplaceContext}
+        >
           <DialogHeader>
             <div className="flex items-center gap-2">
               <VercelLogo className="size-5" />
@@ -787,7 +791,11 @@ export function VercelOnboardingModal({
         }
       }}
     >
-      <DialogContent className="max-w-lg" onInteractOutside={(e) => e.preventDefault()}>
+      <DialogContent
+        className="max-w-lg"
+        onInteractOutside={(e) => e.preventDefault()}
+        showCloseButton={!fromMarketplaceContext}
+      >
         <DialogHeader>
           <div className="flex items-center gap-2">
             <VercelLogo className="size-5" />
diff --git a/apps/webapp/app/components/primitives/Buttons.tsx b/apps/webapp/app/components/primitives/Buttons.tsx
index 78b201b90e0..4a19157d2eb 100644
--- a/apps/webapp/app/components/primitives/Buttons.tsx
+++ b/apps/webapp/app/components/primitives/Buttons.tsx
@@ -397,6 +397,7 @@ export const Button = forwardRef<HTMLButtonElement, ButtonPropsType>(
         }
       },
       disabled: isDisabled || !props.shortcut,
+      elementRef: innerRef,
     });
 
     const buttonElement = (
@@ -467,6 +468,7 @@ export const LinkButton = ({
       }
     },
     disabled: disabled || !props.shortcut,
+    elementRef: innerRef,
   });
 
   if (disabled) {
diff --git a/apps/webapp/app/components/primitives/SearchInput.tsx b/apps/webapp/app/components/primitives/SearchInput.tsx
index 0c46a3d0286..520fa1c6b33 100644
--- a/apps/webapp/app/components/primitives/SearchInput.tsx
+++ b/apps/webapp/app/components/primitives/SearchInput.tsx
@@ -127,7 +127,6 @@ export function SearchInput({
             }
             if (e.key === "Escape") {
               if (text.length > 0) {
-                e.stopPropagation();
                 handleClear();
               } else {
                 e.currentTarget.blur();
diff --git a/apps/webapp/app/components/primitives/SheetV3.tsx b/apps/webapp/app/components/primitives/SheetV3.tsx
index 922f28d5baf..a9a71b8fde5 100644
--- a/apps/webapp/app/components/primitives/SheetV3.tsx
+++ b/apps/webapp/app/components/primitives/SheetV3.tsx
@@ -50,16 +50,42 @@ const sheetVariants = cva(
 interface SheetContentProps
   extends
     React.ComponentPropsWithoutRef<typeof SheetPrimitive.Content>,
-    VariantProps<typeof sheetVariants> {}
+    VariantProps<typeof sheetVariants> {
+  showCloseButton?: boolean;
+}
+
+const SheetCloseButtonContext = React.createContext(false);
+
+/**
+ * True when an enclosing sheet renders its own floating close button, so a header
+ * rendered inside it has to leave room for it. False outside a sheet, which is why
+ * components used both in a sheet and as a full page can rely on it.
+ */
+export function useSheetHasCloseButton() {
+  return React.useContext(SheetCloseButtonContext);
+}
 
 const SheetContent = React.forwardRef<
   React.ElementRef<typeof SheetPrimitive.Content>,
   SheetContentProps
->(({ side = "right", className, children, ...props }, ref) => (
+>(({ side = "right", className, children, showCloseButton = true, ...props }, ref) => (
   <SheetPortal>
     <SheetOverlay />
     <SheetPrimitive.Content ref={ref} className={cn(sheetVariants({ side }), className)} {...props}>
-      {children}
+      {showCloseButton && (
+        // Zero-height sticky wrapper so the button stays pinned to the top right
+        // even when the sheet itself is the scrolling element.
+        <div className="sticky top-0 z-10 h-0">
+          <SheetPrimitive.Close className="absolute right-2 top-2 flex items-center gap-1 rounded-sm p-1 pl-0 transition hover:bg-background-hover focus-visible:focus-custom disabled:pointer-events-none">
+            <ShortcutKey shortcut={{ key: "esc" }} variant="small" />
+            <XMarkIcon className="size-4 text-text-dimmed" />
+            <span className="sr-only">Close</span>
+          </SheetPrimitive.Close>
+        </div>
+      )}
+      <SheetCloseButtonContext.Provider value={showCloseButton}>
+        {children}
+      </SheetCloseButtonContext.Provider>
     </SheetPrimitive.Content>
   </SheetPortal>
 ));
@@ -81,23 +107,23 @@ SheetFooter.displayName = "SheetFooter";
 const SheetTitle = React.forwardRef<
   React.ElementRef<typeof SheetPrimitive.Title>,
   React.ComponentPropsWithoutRef<typeof SheetPrimitive.Title>
->(({ className, children, ...props }, ref) => (
-  <SheetPrimitive.Title
-    ref={ref}
-    className={cn(
-      "sticky top-0 flex items-center justify-between border-b border-grid-bright bg-background-dimmed pb-1.5 pl-3 pr-1.5 pt-2",
-      className
-    )}
-    {...props}
-  >
-    {children}
-    <SheetPrimitive.Close className="flex items-center gap-1 rounded-sm p-1 pl-0 transition hover:bg-background-hover focus-visible:focus-custom disabled:pointer-events-none">
-      <ShortcutKey shortcut={{ key: "esc" }} variant="small" />
-      <XMarkIcon className="size-4 text-text-dimmed" />
-      <span className="sr-only">Close</span>
-    </SheetPrimitive.Close>
-  </SheetPrimitive.Title>
-));
+>(({ className, children, ...props }, ref) => {
+  const hasCloseButton = useSheetHasCloseButton();
+
+  return (
+    <SheetPrimitive.Title
+      ref={ref}
+      className={cn(
+        "sticky top-0 flex items-center justify-between border-b border-grid-bright bg-background-dimmed pb-1.5 pl-3 pt-2",
+        hasCloseButton ? "pr-16" : "pr-1.5",
+        className
+      )}
+      {...props}
+    >
+      {children}
+    </SheetPrimitive.Title>
+  );
+});
 SheetTitle.displayName = SheetPrimitive.Title.displayName;
 
 const SheetDescription = React.forwardRef<
diff --git a/apps/webapp/app/components/schedules/ScheduleInspector.tsx b/apps/webapp/app/components/schedules/ScheduleInspector.tsx
index 1d0de51dc94..dafb5bfbc19 100644
--- a/apps/webapp/app/components/schedules/ScheduleInspector.tsx
+++ b/apps/webapp/app/components/schedules/ScheduleInspector.tsx
@@ -23,6 +23,7 @@ import { Header2, Header3 } from "~/components/primitives/Headers";
 import { InfoPanel } from "~/components/primitives/InfoPanel";
 import { Paragraph } from "~/components/primitives/Paragraph";
 import * as Property from "~/components/primitives/PropertyTable";
+import { useSheetHasCloseButton } from "~/components/primitives/SheetV3";
 import {
   Table,
   TableBlankRow,
@@ -96,6 +97,7 @@ export function ScheduleInspector({
   const organization = useOrganization();
   const project = useProject();
   const environment = useEnvironment();
+  const hasSheetCloseButton = useSheetHasCloseButton();
 
   const isUtc = schedule.timezone === "UTC";
   const isImperative = schedule.type === "IMPERATIVE";
@@ -107,8 +109,13 @@ export function ScheduleInspector({
         isImperative ? "grid-rows-[2.5rem_1fr_auto]" : "grid-rows-[2.5rem_1fr]"
       )}
     >
-      <div className="mx-3 flex items-center justify-between gap-2 border-b border-grid-dimmed">
-        <Header2 className="whitespace-nowrap">{schedule.friendlyId}</Header2>
+      <div
+        className={cn(
+          "mx-3 flex items-center justify-between gap-2 border-b border-grid-dimmed",
+          hasSheetCloseButton && "pr-14"
+        )}
+      >
+        <Header2 className="truncate">{schedule.friendlyId}</Header2>
         {headerActions}
       </div>
       <div className="overflow-y-scroll scrollbar-thin scrollbar-track-transparent scrollbar-thumb-surface-control">
diff --git a/apps/webapp/app/hooks/useShortcutKeys.tsx b/apps/webapp/app/hooks/useShortcutKeys.tsx
index 319a91cad84..d94db224f3d 100644
--- a/apps/webapp/app/hooks/useShortcutKeys.tsx
+++ b/apps/webapp/app/hooks/useShortcutKeys.tsx
@@ -1,3 +1,4 @@
+import { type RefObject } from "react";
 import { useHotkeys } from "react-hotkeys-hook";
 import { useOperatingSystem } from "~/components/primitives/OperatingSystemProvider";
 import { useShortcuts } from "~/components/primitives/ShortcutsProvider";
@@ -22,14 +23,46 @@ type useShortcutKeysProps = {
   shortcut: ShortcutDefinition | undefined;
   action: (event: KeyboardEvent) => void;
   disabled?: boolean;
+  /**
+   * Shortcuts are registered on `document`, so this fires the shortcut from every
+   * input on the page, not just the ones near it. Don't set it on an Escape
+   * close shortcut: let the focused field handle Escape and close on the second press.
+   */
   enabledOnInputElements?: boolean;
+  /**
+   * The element this shortcut belongs to. When set, an Escape shortcut is ignored
+   * while the element sits behind an open overlay, so one Escape can't close both
+   * a dialog and the panel behind it. Other shortcuts are unaffected.
+   */
+  elementRef?: RefObject<HTMLElement | null>;
 };
 
+/** Layered surfaces that own the keyboard while they're open. */
+const OVERLAY_ROLES = '[role="dialog"],[role="alertdialog"],[role="listbox"],[role="menu"]';
+
+const ESCAPE_KEYS = ["esc", "escape"];
+
+function isEscapeShortcut(shortcut: Shortcut | undefined) {
+  return !!shortcut && ESCAPE_KEYS.includes(shortcut.key.toLowerCase());
+}
+
+function isBlockedByOverlay(event: KeyboardEvent, element: HTMLElement | null) {
+  // Radix marks everything outside an open modal `aria-hidden`, which covers
+  // modals that don't move focus into themselves.
+  if (element?.closest('[aria-hidden="true"]')) return true;
+
+  const target = event.target instanceof Element ? event.target : null;
+  const overlay = target?.closest(OVERLAY_ROLES);
+
+  return !!overlay && (!element || !overlay.contains(element));
+}
+
 export function useShortcutKeys({
   shortcut,
   action,
   disabled = false,
   enabledOnInputElements,
+  elementRef,
 }: useShortcutKeysProps) {
   const { platform } = useOperatingSystem();
   const { areShortcutsEnabled } = useShortcuts();
@@ -40,13 +73,17 @@ export function useShortcutKeys({
   const keys = createKeysFromShortcut(relevantShortcut);
 
   const isEnabled = !disabled && areShortcutsEnabled && relevantShortcut?.enabled !== false;
+  const guardAgainstOverlays = isEscapeShortcut(relevantShortcut);
 
   useHotkeys(
     keys,
     (event) => {
-      if (!event.repeat) {
-        action(event);
+      if (event.repeat) return;
+      if (guardAgainstOverlays && elementRef && isBlockedByOverlay(event, elementRef.current)) {
+        return;
       }
+
+      action(event);
     },
     {
       enabled: isEnabled,
diff --git a/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.dashboards.custom.$dashboardId/route.tsx b/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.dashboards.custom.$dashboardId/route.tsx
index 0a1b448564f..f65507e8dfa 100644
--- a/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.dashboards.custom.$dashboardId/route.tsx
+++ b/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.dashboards.custom.$dashboardId/route.tsx
@@ -569,6 +569,8 @@ export default function Page() {
         <SheetContent
           side="right"
           className="w-[90vw] max-w-none rounded-l-lg border-l border-grid-dimmed p-0 sm:max-w-none"
+          // The editor's own nav bar already has an Esc-labelled Cancel button there.
+          showCloseButton={false}
         >
           {editorProps && (
             <QueryEditor
diff --git a/apps/webapp/app/routes/resources.account.mfa.setup/MfaSetupDialog.tsx b/apps/webapp/app/routes/resources.account.mfa.setup/MfaSetupDialog.tsx
index 3f5bb9ff367..d40e394f8fa 100644
--- a/apps/webapp/app/routes/resources.account.mfa.setup/MfaSetupDialog.tsx
+++ b/apps/webapp/app/routes/resources.account.mfa.setup/MfaSetupDialog.tsx
@@ -75,6 +75,8 @@ export function MfaSetupDialog({
 
   // Show recovery codes if they exist
   if (recoveryCodes && recoveryCodes.length > 0) {
+    // Deliberately not dismissible: MFA is already enabled at this point and the
+    // codes are shown once, so the only way out is confirming they're saved.
     return (
       <Dialog open={isOpen}>
         <DialogContent showCloseButton={false}>
@@ -136,8 +138,8 @@ export function MfaSetupDialog({
   if (!setupData) return null;
 
   return (
-    <Dialog open={isOpen}>
-      <DialogContent showCloseButton={false}>
+    <Dialog open={isOpen} onOpenChange={(open) => !open && handleCancel()}>
+      <DialogContent onInteractOutside={(e) => e.preventDefault()}>
         <DialogHeader>
           <DialogTitle>Enable authenticator app</DialogTitle>
         </DialogHeader>
diff --git a/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.schedules.new/route.tsx b/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.schedules.new/route.tsx
index 61ce814dbd5..afd04d46fc9 100644
--- a/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.schedules.new/route.tsx
+++ b/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.schedules.new/route.tsx
@@ -40,6 +40,7 @@ import {
   TableRow,
 } from "~/components/primitives/Table";
 import { TextLink } from "~/components/primitives/TextLink";
+import { useSheetHasCloseButton } from "~/components/primitives/SheetV3";
 import { TimezoneList } from "~/components/scheduled/timezones";
 import { prisma } from "~/db.server";
 import { useEnvironment } from "~/hooks/useEnvironment";
@@ -156,6 +157,7 @@ export function UpsertScheduleForm({
   /** Submits via this fetcher with `_format=json` so the host can toast/close itself. */
   submitFetcher?: FetcherWithComponents<unknown>;
 }) {
+  const hasSheetCloseButton = useSheetHasCloseButton();
   const actionData = useActionData();
   // Only feed conform-shaped data (`status`) to `useForm` — `{ ok, message }`
   // envelopes lack it and crash conform.
@@ -231,7 +233,12 @@ export function UpsertScheduleForm({
       {...getFormProps(form)}
       className="grid h-full max-h-full grid-rows-[2.5rem_1fr_auto] overflow-hidden bg-background-bright"
     >
-      <div className="mx-3 flex min-w-0 items-center justify-between gap-2 overflow-hidden border-b border-grid-dimmed">
+      <div
+        className={cn(
+          "mx-3 flex min-w-0 items-center justify-between gap-2 overflow-hidden border-b border-grid-dimmed",
+          hasSheetCloseButton && "pr-14"
+        )}
+      >
         <Header2 className="truncate">
           {schedule?.friendlyId
             ? "Edit schedule"