diff --git a/apps/web/src/components/BranchToolbarBranchSelector.tsx b/apps/web/src/components/BranchToolbarBranchSelector.tsx
index ed8f1cd1f026..3bab1315ee8b 100644
--- a/apps/web/src/components/BranchToolbarBranchSelector.tsx
+++ b/apps/web/src/components/BranchToolbarBranchSelector.tsx
@@ -918,7 +918,7 @@ export function BranchToolbarBranchSelector({
                   </label>
                 }
               />
-              <TooltipPopup side="top" className="max-w-72 whitespace-normal leading-tight">
+              <TooltipPopup side="top">
                 Creates the worktree from the latest matching branch on origin instead of your local
                 branch.
               </TooltipPopup>
diff --git a/apps/web/src/components/ChatMarkdown.tsx b/apps/web/src/components/ChatMarkdown.tsx
index 90fca5356804..fe7859968bea 100644
--- a/apps/web/src/components/ChatMarkdown.tsx
+++ b/apps/web/src/components/ChatMarkdown.tsx
@@ -2209,10 +2209,7 @@ const MarkdownFileLink = memo(function MarkdownFileLink({
           )
         }
       />
-      <TooltipPopup
-        side="top"
-        className="max-w-[min(40rem,calc(100vw-2rem))] font-mono text-[11px] leading-tight"
-      >
+      <TooltipPopup side="top" variant="code">
         {/* The full path: the chip already shows the shortened form, and a link
             to the workspace root collapses to a bare label that repeats it. */}
         <div className="overflow-x-auto whitespace-nowrap [scrollbar-color:color-mix(in_srgb,var(--contrast-border)_78%,transparent)_transparent] [scrollbar-width:thin] [&::-webkit-scrollbar]:h-1.5 [&::-webkit-scrollbar-thumb]:rounded-full [&::-webkit-scrollbar-thumb]:bg-[color-mix(in_srgb,var(--contrast-border)_78%,transparent)] [&::-webkit-scrollbar-track]:bg-transparent">
@@ -3062,12 +3059,7 @@ const CHAT_MARKDOWN_COMPONENTS = {
       return (
         <Tooltip>
           <TooltipTrigger render={link} />
-          <TooltipPopup
-            side="top"
-            className="max-w-[min(36rem,calc(100vw-2rem))] whitespace-normal leading-tight wrap-anywhere"
-          >
-            {href}
-          </TooltipPopup>
+          <TooltipPopup side="top">{href}</TooltipPopup>
         </Tooltip>
       );
     }
diff --git a/apps/web/src/components/ChatView.tsx b/apps/web/src/components/ChatView.tsx
index 0d0810eefa42..b97411e7a44b 100644
--- a/apps/web/src/components/ChatView.tsx
+++ b/apps/web/src/components/ChatView.tsx
@@ -6533,7 +6533,7 @@ export default function ChatView(props: ChatViewProps) {
                   </code>
                 }
               />
-              <TooltipPopup side="top" className="max-w-80">
+              <TooltipPopup side="top">
                 This thread last ran on {localCheckoutBranchMismatch.threadBranch}. Sending will
                 continue on {localCheckoutBranchMismatch.currentBranch}.
               </TooltipPopup>
diff --git a/apps/web/src/components/ComposerPromptEditorTiptap.tsx b/apps/web/src/components/ComposerPromptEditorTiptap.tsx
index 0e452fd4ac26..ec9b9e07e2fb 100644
--- a/apps/web/src/components/ComposerPromptEditorTiptap.tsx
+++ b/apps/web/src/components/ComposerPromptEditorTiptap.tsx
@@ -237,12 +237,7 @@ function ComposerMentionNodeView({ node }: NodeViewProps) {
     <NodeViewWrapper as="span" className={COMPOSER_INLINE_CHIP_DECORATOR_CLASS_NAME}>
       <Tooltip>
         <TooltipTrigger render={chip} />
-        <TooltipPopup
-          side="top"
-          className="max-w-120 whitespace-normal leading-tight wrap-anywhere"
-        >
-          {path}
-        </TooltipPopup>
+        <TooltipPopup side="top">{path}</TooltipPopup>
       </Tooltip>
     </NodeViewWrapper>
   );
diff --git a/apps/web/src/components/ConfirmDialogHost.tsx b/apps/web/src/components/ConfirmDialogHost.tsx
index 3e19606bd4c6..92477801eb72 100644
--- a/apps/web/src/components/ConfirmDialogHost.tsx
+++ b/apps/web/src/components/ConfirmDialogHost.tsx
@@ -77,7 +77,7 @@ export function ConfirmDialogHost() {
     >
       <AlertDialogPopup>
         <AlertDialogHeader>
-          <AlertDialogTitle className="wrap-anywhere">{copy.title}</AlertDialogTitle>
+          <AlertDialogTitle>{copy.title}</AlertDialogTitle>
           {copy.description ? (
             <AlertDialogDescription className="whitespace-pre-line">
               {copy.description}
diff --git a/apps/web/src/components/ConnectionStatusDot.tsx b/apps/web/src/components/ConnectionStatusDot.tsx
index 6a23a0532873..b371b6c1fe97 100644
--- a/apps/web/src/components/ConnectionStatusDot.tsx
+++ b/apps/web/src/components/ConnectionStatusDot.tsx
@@ -69,7 +69,7 @@ export function ConnectionStatusDot({
   return (
     <Tooltip>
       <TooltipTrigger render={dot} />
-      <TooltipPopup side="top" className="max-w-80 whitespace-pre-wrap leading-tight">
+      <TooltipPopup side="top" className="whitespace-pre-wrap">
         {tooltipText}
       </TooltipPopup>
     </Tooltip>
diff --git a/apps/web/src/components/GitActionsControl.tsx b/apps/web/src/components/GitActionsControl.tsx
index 4eca7867132e..c849532dafdb 100644
--- a/apps/web/src/components/GitActionsControl.tsx
+++ b/apps/web/src/components/GitActionsControl.tsx
@@ -659,7 +659,7 @@ function PublishRepositoryDialog(props: PublishRepositoryDialogProps) {
                             </Button>
                           }
                         />
-                        <TooltipPopup side="top" align="end" className="max-w-72">
+                        <TooltipPopup side="top" align="end">
                           {readiness.hint ??
                             "Open Settings -> Source Control to configure this provider."}
                         </TooltipPopup>
diff --git a/apps/web/src/components/LegacySidebar.tsx b/apps/web/src/components/LegacySidebar.tsx
index b4b686a0c11d..b98f3a30ed26 100644
--- a/apps/web/src/components/LegacySidebar.tsx
+++ b/apps/web/src/components/LegacySidebar.tsx
@@ -785,9 +785,7 @@ const SidebarThreadRow = memo(function SidebarThreadRow(props: SidebarThreadRowP
                   </span>
                 }
               />
-              <TooltipPopup side="top" className="max-w-80 whitespace-normal leading-tight">
-                {thread.title}
-              </TooltipPopup>
+              <TooltipPopup side="top">{thread.title}</TooltipPopup>
             </Tooltip>
           )}
         </div>
diff --git a/apps/web/src/components/ServerUpdateAction.tsx b/apps/web/src/components/ServerUpdateAction.tsx
index 288078729d5d..a4b288a6eab7 100644
--- a/apps/web/src/components/ServerUpdateAction.tsx
+++ b/apps/web/src/components/ServerUpdateAction.tsx
@@ -163,9 +163,7 @@ export function ServerUpdateProgress({
         <span className="size-1.5 shrink-0 rounded-full bg-destructive" aria-hidden="true" />
         <Tooltip>
           <TooltipTrigger render={<span className="min-w-0 truncate">{state.message}</span>} />
-          <TooltipPopup side="top" className="max-w-80">
-            {state.message}
-          </TooltipPopup>
+          <TooltipPopup side="top">{state.message}</TooltipPopup>
         </Tooltip>
       </div>
     );
diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index 022024eadcc8..799ab3f9e545 100644
--- a/apps/web/src/components/Sidebar.tsx
+++ b/apps/web/src/components/Sidebar.tsx
@@ -350,7 +350,7 @@ function SidebarThreadTooltip({
       align="start"
       sideOffset={4}
       variant="glass"
-      className="max-w-80 text-left whitespace-normal [&_[data-slot=tooltip-viewport]]:p-0"
+      className="[&_[data-slot=tooltip-viewport]]:p-0"
     >
       <div className="flex min-w-0 max-w-80 flex-col gap-2 p-[var(--floating-content-inset)]">
         <div className="min-w-0 truncate text-xs leading-tight font-medium text-foreground">
diff --git a/apps/web/src/components/StartTruncatedPath.tsx b/apps/web/src/components/StartTruncatedPath.tsx
index b467d141a8ca..60cb6cdc740d 100644
--- a/apps/web/src/components/StartTruncatedPath.tsx
+++ b/apps/web/src/components/StartTruncatedPath.tsx
@@ -17,7 +17,7 @@ export function StartTruncatedPath({ path, className }: { path: string; classNam
       >
         <bdi>{path}</bdi>
       </TooltipTrigger>
-      <TooltipPopup side="top" className="max-w-sm break-all font-mono">
+      <TooltipPopup side="top" variant="code">
         {path}
       </TooltipPopup>
     </Tooltip>
diff --git a/apps/web/src/components/chat/ChatComposer.tsx b/apps/web/src/components/chat/ChatComposer.tsx
index f1de1f81434e..101dbcb4af25 100644
--- a/apps/web/src/components/chat/ChatComposer.tsx
+++ b/apps/web/src/components/chat/ChatComposer.tsx
@@ -6569,10 +6569,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
                                     </span>
                                   }
                                 />
-                                <TooltipPopup
-                                  side="top"
-                                  className="max-w-64 whitespace-normal leading-tight"
-                                >
+                                <TooltipPopup side="top">
                                   Draft attachment could not be saved locally and may be lost on
                                   navigation.
                                 </TooltipPopup>
@@ -6604,12 +6601,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
                                 >
                                   <RefreshIcon />
                                 </TooltipTrigger>
-                                <TooltipPopup
-                                  side="top"
-                                  className="max-w-64 whitespace-normal leading-tight"
-                                >
-                                  {upload.reason}
-                                </TooltipPopup>
+                                <TooltipPopup side="top">{upload.reason}</TooltipPopup>
                               </Tooltip>
                             )}
                             <Button
@@ -6704,12 +6696,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
                               >
                                 <RefreshIcon />
                               </TooltipTrigger>
-                              <TooltipPopup
-                                side="top"
-                                className="max-w-64 whitespace-normal leading-tight"
-                              >
-                                {upload.reason}
-                              </TooltipPopup>
+                              <TooltipPopup side="top">{upload.reason}</TooltipPopup>
                             </Tooltip>
                           )}
                           <Button
@@ -6787,12 +6774,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
                               >
                                 <RefreshIcon />
                               </TooltipTrigger>
-                              <TooltipPopup
-                                side="top"
-                                className="max-w-64 whitespace-normal leading-tight"
-                              >
-                                {upload.reason}
-                              </TooltipPopup>
+                              <TooltipPopup side="top">{upload.reason}</TooltipPopup>
                             </Tooltip>
                           ) : null}
                           <Button
diff --git a/apps/web/src/components/chat/ComposerPendingApprovalActions.tsx b/apps/web/src/components/chat/ComposerPendingApprovalActions.tsx
index 743d846dc5e2..cebdf7d1cd50 100644
--- a/apps/web/src/components/chat/ComposerPendingApprovalActions.tsx
+++ b/apps/web/src/components/chat/ComposerPendingApprovalActions.tsx
@@ -59,9 +59,7 @@ export const ComposerPendingApprovalActions = memo(function ComposerPendingAppro
         return option.warning ? (
           <Tooltip key={option.decision}>
             <TooltipTrigger render={button} />
-            <TooltipPopup side="top" className="max-w-72 text-xs leading-snug">
-              {option.warning}
-            </TooltipPopup>
+            <TooltipPopup side="top">{option.warning}</TooltipPopup>
           </Tooltip>
         ) : (
           button
@@ -98,9 +96,7 @@ export const ComposerPendingApprovalActions = memo(function ComposerPendingAppro
               return option.warning ? (
                 <Tooltip key={option.decision}>
                   <TooltipTrigger render={item} />
-                  <TooltipPopup side="top" className="max-w-64 text-xs leading-snug">
-                    {option.warning}
-                  </TooltipPopup>
+                  <TooltipPopup side="top">{option.warning}</TooltipPopup>
                 </Tooltip>
               ) : (
                 item
diff --git a/apps/web/src/components/chat/ComposerServerUpdateStatus.tsx b/apps/web/src/components/chat/ComposerServerUpdateStatus.tsx
index 7431932ce9a9..f871a5aab19e 100644
--- a/apps/web/src/components/chat/ComposerServerUpdateStatus.tsx
+++ b/apps/web/src/components/chat/ComposerServerUpdateStatus.tsx
@@ -56,7 +56,7 @@ export function ComposerServerUpdateStatus({
             </button>
           }
         />
-        <TooltipPopup side="top" className="max-w-80">
+        <TooltipPopup side="top">
           {title}: {detail}
         </TooltipPopup>
       </Tooltip>
diff --git a/apps/web/src/components/chat/DraftHeroHeadline.tsx b/apps/web/src/components/chat/DraftHeroHeadline.tsx
index d542cd6a8a9f..89f5c103d0a6 100644
--- a/apps/web/src/components/chat/DraftHeroHeadline.tsx
+++ b/apps/web/src/components/chat/DraftHeroHeadline.tsx
@@ -146,9 +146,7 @@ export function DraftHeroHeadline({
           {activeProjectDisplayName ?? "Choose a project"}
         </TooltipTrigger>
         {activeProjectDisplayName ? (
-          <TooltipPopup side="top" className="max-w-80">
-            {activeProjectDisplayName}
-          </TooltipPopup>
+          <TooltipPopup side="top">{activeProjectDisplayName}</TooltipPopup>
         ) : null}
       </Tooltip>
       <MenuPopup align="center" className="max-h-80 min-w-40! w-max max-w-64 overflow-y-auto">
@@ -202,9 +200,7 @@ export function DraftHeroHeadline({
                   <TooltipTrigger render={<span className="block min-w-0 truncate" />}>
                     {group.displayName}
                   </TooltipTrigger>
-                  <TooltipPopup side="top" className="max-w-80">
-                    {group.displayName}
-                  </TooltipPopup>
+                  <TooltipPopup side="top">{group.displayName}</TooltipPopup>
                 </Tooltip>
                 {showProjectEnvironments ? (
                   <ProjectEnvironmentBadge
diff --git a/apps/web/src/components/chat/ModelListRow.tsx b/apps/web/src/components/chat/ModelListRow.tsx
index 5917b4e2ca24..1d05374035be 100644
--- a/apps/web/src/components/chat/ModelListRow.tsx
+++ b/apps/web/src/components/chat/ModelListRow.tsx
@@ -145,7 +145,7 @@ export const ModelListRow = memo(function ModelListRow(props: {
   return (
     <Tooltip>
       <TooltipTrigger render={row} />
-      <TooltipPopup side="left" align="center" className="max-w-64 text-balance leading-snug">
+      <TooltipPopup side="left" align="center">
         {props.disabledReason}
       </TooltipPopup>
     </Tooltip>
diff --git a/apps/web/src/components/chat/ModelPickerSidebar.tsx b/apps/web/src/components/chat/ModelPickerSidebar.tsx
index 19a542d2aa2f..93d2b2726770 100644
--- a/apps/web/src/components/chat/ModelPickerSidebar.tsx
+++ b/apps/web/src/components/chat/ModelPickerSidebar.tsx
@@ -39,7 +39,6 @@ const NEW_BADGE_CLASS = `${BADGE_BASE_CLASS} text-update-foreground `;
 /** Opens toward the rail so the list stays readable (not over the model names). */
 const PICKER_TOOLTIP_SIDE = "left" as const;
 const PICKER_TOOLTIP_SIDE_OFFSET = 8;
-const PICKER_TOOLTIP_CLASS = "max-w-64 text-balance font-normal leading-snug";
 
 export const ModelPickerSidebar = memo(function ModelPickerSidebar(props: {
   selectedInstanceId: ProviderInstanceId | "favorites";
@@ -139,7 +138,6 @@ export const ModelPickerSidebar = memo(function ModelPickerSidebar(props: {
                     side={PICKER_TOOLTIP_SIDE}
                     sideOffset={PICKER_TOOLTIP_SIDE_OFFSET}
                     align="center"
-                    className={PICKER_TOOLTIP_CLASS}
                   >
                     Favorites
                   </TooltipPopup>
@@ -242,7 +240,6 @@ export const ModelPickerSidebar = memo(function ModelPickerSidebar(props: {
                     side={PICKER_TOOLTIP_SIDE}
                     sideOffset={PICKER_TOOLTIP_SIDE_OFFSET}
                     align="center"
-                    className={PICKER_TOOLTIP_CLASS}
                   >
                     {tooltip}
                   </TooltipPopup>
diff --git a/apps/web/src/components/chat/ProviderStatusBanner.tsx b/apps/web/src/components/chat/ProviderStatusBanner.tsx
index 210bff4d7ad4..9e84fc01c920 100644
--- a/apps/web/src/components/chat/ProviderStatusBanner.tsx
+++ b/apps/web/src/components/chat/ProviderStatusBanner.tsx
@@ -100,7 +100,7 @@ export const ProviderStatusBanner = memo(function ProviderStatusBanner({
             <TooltipTrigger
               render={<div className="line-clamp-3 text-muted-foreground">{message}</div>}
             />
-            <TooltipPopup side="top" className="max-w-96 whitespace-pre-wrap">
+            <TooltipPopup side="top" className="whitespace-pre-wrap">
               {message}
             </TooltipPopup>
           </Tooltip>
diff --git a/apps/web/src/components/chat/ThreadErrorBanner.tsx b/apps/web/src/components/chat/ThreadErrorBanner.tsx
index 29a6a6db1846..df01506ba9ee 100644
--- a/apps/web/src/components/chat/ThreadErrorBanner.tsx
+++ b/apps/web/src/components/chat/ThreadErrorBanner.tsx
@@ -53,7 +53,7 @@ export const ThreadErrorBanner = memo(function ThreadErrorBanner({
         <AlertDescription>
           <Tooltip>
             <TooltipTrigger render={<div className="line-clamp-3" />}>{error}</TooltipTrigger>
-            <TooltipPopup side="top" className="max-w-96 whitespace-pre-wrap">
+            <TooltipPopup side="top" className="whitespace-pre-wrap">
               {error}
             </TooltipPopup>
           </Tooltip>
diff --git a/apps/web/src/components/cloud/CloudEnvironmentConnectList.tsx b/apps/web/src/components/cloud/CloudEnvironmentConnectList.tsx
index de054d0a5d29..5022031e98e6 100644
--- a/apps/web/src/components/cloud/CloudEnvironmentConnectList.tsx
+++ b/apps/web/src/components/cloud/CloudEnvironmentConnectList.tsx
@@ -393,9 +393,7 @@ export function CloudEnvironmentConnectRows({
                         ? "Unavailable"
                         : "Checking…"))}
             </TooltipTrigger>
-            <TooltipPopup className="max-w-80 break-words">
-              {unsupportedDetail ?? statusText}
-            </TooltipPopup>
+            <TooltipPopup>{unsupportedDetail ?? statusText}</TooltipPopup>
           </Tooltip>
         </label>
       );
@@ -454,9 +452,7 @@ export function CloudEnvironmentConnectRows({
                   Add
                 </Button>
               </TooltipTrigger>
-              <TooltipPopup className="max-w-80 break-words">
-                {unsupportedDetail ?? "Client not supported"}
-              </TooltipPopup>
+              <TooltipPopup>{unsupportedDetail ?? "Client not supported"}</TooltipPopup>
             </Tooltip>
           ) : savedConnection ? (
             <Button size="sm" variant="outline" disabled>
diff --git a/apps/web/src/components/composerContextPresentation.tsx b/apps/web/src/components/composerContextPresentation.tsx
index 9e5c775161cb..9c86b47581f0 100644
--- a/apps/web/src/components/composerContextPresentation.tsx
+++ b/apps/web/src/components/composerContextPresentation.tsx
@@ -199,7 +199,7 @@ function ImageContextChip(props: {
           />
         }
       />
-      <TooltipPopup side="top" className="max-w-80 whitespace-pre-wrap leading-tight">
+      <TooltipPopup side="top" className="whitespace-pre-wrap">
         {attachmentTooltip(props.record, props.upload)}
       </TooltipPopup>
     </Tooltip>
diff --git a/apps/web/src/components/contextChipParts.tsx b/apps/web/src/components/contextChipParts.tsx
index f0a47b22e3c3..691fd2ec33c2 100644
--- a/apps/web/src/components/contextChipParts.tsx
+++ b/apps/web/src/components/contextChipParts.tsx
@@ -301,7 +301,7 @@ export function FileChip(props: {
           )
         }
       />
-      <TooltipPopup side="top" className="max-w-80 whitespace-pre-wrap leading-tight">
+      <TooltipPopup side="top" className="whitespace-pre-wrap">
         {props.tooltip}
       </TooltipPopup>
     </Tooltip>
diff --git a/apps/web/src/components/files/FileBreadcrumbs.tsx b/apps/web/src/components/files/FileBreadcrumbs.tsx
index aa7bc97be0f9..01bec38f343e 100644
--- a/apps/web/src/components/files/FileBreadcrumbs.tsx
+++ b/apps/web/src/components/files/FileBreadcrumbs.tsx
@@ -61,9 +61,7 @@ function BreadcrumbLabel(props: {
       >
         {props.label}
       </TooltipTrigger>
-      <TooltipPopup side="top" className="max-w-80">
-        {props.pathLabel}
-      </TooltipPopup>
+      <TooltipPopup side="top">{props.pathLabel}</TooltipPopup>
     </Tooltip>
   );
 }
@@ -241,9 +239,7 @@ function DirectoryBreadcrumb(props: FileBreadcrumbsProps & { readonly crumb: Fil
         >
           <span className="block truncate">{props.crumb.label}</span>
         </TooltipTrigger>
-        <TooltipPopup side="top" className="max-w-80">
-          {props.crumb.path || props.projectName}
-        </TooltipPopup>
+        <TooltipPopup side="top">{props.crumb.path || props.projectName}</TooltipPopup>
       </Tooltip>
       {open ? (
         <BreadcrumbMenuContent
diff --git a/apps/web/src/components/media/MediaActions.tsx b/apps/web/src/components/media/MediaActions.tsx
index d6c5cca70153..d4e96c5445b4 100644
--- a/apps/web/src/components/media/MediaActions.tsx
+++ b/apps/web/src/components/media/MediaActions.tsx
@@ -186,9 +186,7 @@ export function MediaActions({
           void showMenu({ x: bounds.left, y: bounds.bottom });
         }}
       />
-      <TooltipPopup className="max-w-[min(40rem,calc(100vw-2rem))] break-all font-mono text-[11px] leading-tight">
-        {tooltip}
-      </TooltipPopup>
+      <TooltipPopup variant="code">{tooltip}</TooltipPopup>
     </Tooltip>
   );
 }
diff --git a/apps/web/src/components/onboarding/WelcomeWizard.tsx b/apps/web/src/components/onboarding/WelcomeWizard.tsx
index 99e0e8513e84..1d4b9662a260 100644
--- a/apps/web/src/components/onboarding/WelcomeWizard.tsx
+++ b/apps/web/src/components/onboarding/WelcomeWizard.tsx
@@ -1453,7 +1453,7 @@ function ImportCandidateRow({
             </span>
           ) : null}
         </TooltipTrigger>
-        <TooltipPopup className="max-w-96 break-all font-mono">{candidate.path}</TooltipPopup>
+        <TooltipPopup variant="code">{candidate.path}</TooltipPopup>
       </Tooltip>
       <ImportRowMeta
         sources={nested ? null : candidate.sources}
diff --git a/apps/web/src/components/pullRequest/PullRequestCopyableCode.tsx b/apps/web/src/components/pullRequest/PullRequestCopyableCode.tsx
index 4c9d14b53734..bcfb3b180113 100644
--- a/apps/web/src/components/pullRequest/PullRequestCopyableCode.tsx
+++ b/apps/web/src/components/pullRequest/PullRequestCopyableCode.tsx
@@ -58,7 +58,7 @@ export function PullRequestCopyableCode({
           Copied
         </span>
       </TooltipTrigger>
-      <TooltipPopup className="max-w-96 wrap-anywhere font-mono" side={tooltipSide}>
+      <TooltipPopup variant="code" side={tooltipSide}>
         {`${isCopied ? "Copied" : copyLabel}: ${value}`}
       </TooltipPopup>
     </Tooltip>
diff --git a/apps/web/src/components/pullRequest/PullRequestListFilters.tsx b/apps/web/src/components/pullRequest/PullRequestListFilters.tsx
index 702584237e70..f769dd70fa4b 100644
--- a/apps/web/src/components/pullRequest/PullRequestListFilters.tsx
+++ b/apps/web/src/components/pullRequest/PullRequestListFilters.tsx
@@ -202,9 +202,7 @@ function PullRequestFilterRadioGroup<Value extends string>({
         return (
           <Tooltip key={option.value}>
             <TooltipTrigger render={item} />
-            <TooltipPopup side="top" className="max-w-80">
-              {option.unavailable}
-            </TooltipPopup>
+            <TooltipPopup side="top">{option.unavailable}</TooltipPopup>
           </Tooltip>
         );
       })}
diff --git a/apps/web/src/components/settings/ConnectionsSettings.tsx b/apps/web/src/components/settings/ConnectionsSettings.tsx
index 1d0b3e0b71f3..0e2213039cc9 100644
--- a/apps/web/src/components/settings/ConnectionsSettings.tsx
+++ b/apps/web/src/components/settings/ConnectionsSettings.tsx
@@ -925,9 +925,7 @@ const PairingLinkListRow = memo(function PairingLinkListRow({
                     </code>
                   }
                 />
-                <TooltipPopup side="top" className="max-w-80 break-all">
-                  {qrPairingUrl}
-                </TooltipPopup>
+                <TooltipPopup side="top">{qrPairingUrl}</TooltipPopup>
               </Tooltip>
               <Button
                 size="xs"
@@ -1334,9 +1332,7 @@ const AdvertisedEndpointListRow = memo(function AdvertisedEndpointListRow({
                   </p>
                 }
               />
-              <TooltipPopup side="top" className="max-w-80">
-                {endpoint.httpBaseUrl}
-              </TooltipPopup>
+              <TooltipPopup side="top">{endpoint.httpBaseUrl}</TooltipPopup>
             </Tooltip>
           ) : null}
           {!isAvailable ? (
@@ -1573,7 +1569,7 @@ function SavedBackendListRow({
           >
             {subtitleText}
           </TooltipTrigger>
-          <TooltipPopup side="top" className="max-w-80 whitespace-pre-wrap leading-tight">
+          <TooltipPopup side="top" className="whitespace-pre-wrap">
             {unsupported
               ? (environment.connection.error ?? connectionStatusText(environment.connection))
               : enabled
@@ -3635,9 +3631,7 @@ export function ConnectionsSettings() {
                       }
                     />
                     {pendingTailscaleServeBaseUrl ? (
-                      <TooltipPopup side="top" className="max-w-80">
-                        {pendingTailscaleServeBaseUrl}
-                      </TooltipPopup>
+                      <TooltipPopup side="top">{pendingTailscaleServeBaseUrl}</TooltipPopup>
                     ) : null}
                   </Tooltip>
                 </div>
diff --git a/apps/web/src/components/settings/DiagnosticsSettings.tsx b/apps/web/src/components/settings/DiagnosticsSettings.tsx
index 0fe1ae2f624e..15fa80237da9 100644
--- a/apps/web/src/components/settings/DiagnosticsSettings.tsx
+++ b/apps/web/src/components/settings/DiagnosticsSettings.tsx
@@ -109,12 +109,7 @@ function StatBlock({
                 </button>
               }
             />
-            <TooltipPopup
-              side="top"
-              className="max-w-[min(300px,calc(100vw-2rem))] whitespace-normal text-left text-[11px] leading-relaxed text-wrap"
-            >
-              {tooltip}
-            </TooltipPopup>
+            <TooltipPopup side="top">{tooltip}</TooltipPopup>
           </Tooltip>
         ) : null}
       </div>
@@ -225,10 +220,7 @@ function TraceIdCell({ traceId }: { traceId: string }) {
             </span>
           }
         />
-        <TooltipPopup
-          side="top"
-          className="max-w-[min(520px,calc(100vw-2rem))] break-all font-mono text-[11px]"
-        >
+        <TooltipPopup side="top" variant="code">
           {traceId}
         </TooltipPopup>
       </Tooltip>
@@ -300,10 +292,7 @@ function ProcessNameCell({
         <TooltipTrigger
           render={<span className="min-w-0 truncate font-medium text-foreground">{name}</span>}
         />
-        <TooltipPopup
-          side="top"
-          className="max-w-[min(440px,calc(100vw-2rem))] whitespace-normal break-words text-left font-mono text-[11px] leading-relaxed text-wrap"
-        >
+        <TooltipPopup side="top" variant="code">
           {process.command}
         </TooltipPopup>
       </Tooltip>
@@ -411,10 +400,7 @@ function ProcessDiagnosticsTable({
                   <TooltipTrigger
                     render={<span className="block truncate">{process.command}</span>}
                   />
-                  <TooltipPopup
-                    side="top"
-                    className="max-w-[min(440px,calc(100vw-2rem))] whitespace-normal break-words text-left font-mono text-[11px] leading-relaxed text-wrap"
-                  >
+                  <TooltipPopup side="top" variant="code">
                     {process.command}
                   </TooltipPopup>
                 </Tooltip>
@@ -484,10 +470,7 @@ function ResourceHistoryProcessNameCell({
         <TooltipTrigger
           render={<span className="min-w-0 truncate font-medium text-foreground">{name}</span>}
         />
-        <TooltipPopup
-          side="top"
-          className="max-w-[min(440px,calc(100vw-2rem))] whitespace-normal break-words text-left font-mono text-[11px] leading-relaxed text-wrap"
-        >
+        <TooltipPopup side="top" variant="code">
           {process.command}
         </TooltipPopup>
       </Tooltip>
@@ -654,10 +637,7 @@ function ProcessResourceHistoryTable({
                   <TooltipTrigger
                     render={<span className="block truncate">{process.command}</span>}
                   />
-                  <TooltipPopup
-                    side="top"
-                    className="max-w-[min(440px,calc(100vw-2rem))] whitespace-normal break-words text-left font-mono text-[11px] leading-relaxed text-wrap"
-                  >
+                  <TooltipPopup side="top" variant="code">
                     {process.command}
                   </TooltipPopup>
                 </Tooltip>
diff --git a/apps/web/src/components/settings/KeybindingsSettings.tsx b/apps/web/src/components/settings/KeybindingsSettings.tsx
index 7c5bbfa65fbe..57f9fff4d4aa 100644
--- a/apps/web/src/components/settings/KeybindingsSettings.tsx
+++ b/apps/web/src/components/settings/KeybindingsSettings.tsx
@@ -261,9 +261,7 @@ function WarningTooltipIcon({
       >
         <TriangleAlertIcon className="size-3.5" />
       </TooltipTrigger>
-      <TooltipPopup side="top" className="max-w-72 whitespace-normal leading-relaxed">
-        {children}
-      </TooltipPopup>
+      <TooltipPopup side="top">{children}</TooltipPopup>
     </Tooltip>
   );
 }
diff --git a/apps/web/src/components/settings/ResourceTelemetryDiagnostics.tsx b/apps/web/src/components/settings/ResourceTelemetryDiagnostics.tsx
index 51cabd6010bc..36326958550d 100644
--- a/apps/web/src/components/settings/ResourceTelemetryDiagnostics.tsx
+++ b/apps/web/src/components/settings/ResourceTelemetryDiagnostics.tsx
@@ -503,10 +503,7 @@ function ProcessTreeName({
         <TooltipTrigger
           render={<span className="min-w-0 truncate font-medium text-foreground">{name}</span>}
         />
-        <TooltipPopup
-          side="top"
-          className="max-w-[min(520px,calc(100vw-2rem))] whitespace-normal break-words text-left font-mono text-[11px]"
-        >
+        <TooltipPopup side="top" variant="code">
           {process.command || process.name}
         </TooltipPopup>
       </Tooltip>
@@ -721,10 +718,7 @@ function HistoryProcessTable({
                       </span>
                     }
                   />
-                  <TooltipPopup
-                    side="top"
-                    className="max-w-[min(520px,calc(100vw-2rem))] whitespace-normal break-words text-left font-mono text-[11px]"
-                  >
+                  <TooltipPopup side="top" variant="code">
                     {process.command || process.name}
                   </TooltipPopup>
                 </Tooltip>
diff --git a/apps/web/src/components/settings/settingsLayout.tsx b/apps/web/src/components/settings/settingsLayout.tsx
index 6691b93a7242..c204fb9d6b65 100644
--- a/apps/web/src/components/settings/settingsLayout.tsx
+++ b/apps/web/src/components/settings/settingsLayout.tsx
@@ -156,9 +156,7 @@ export function PolicyTooltip({ children }: { readonly children: string }) {
           </Button>
         }
       />
-      <TooltipPopup side="top" className="max-w-72">
-        {children}
-      </TooltipPopup>
+      <TooltipPopup side="top">{children}</TooltipPopup>
     </Tooltip>
   );
 }
@@ -372,9 +370,7 @@ export function SettingsRow({
           {control}
         </div>
       </TooltipTrigger>
-      <TooltipPopup side="top" className="max-w-72">
-        {message}
-      </TooltipPopup>
+      <TooltipPopup side="top">{message}</TooltipPopup>
     </Tooltip>
   );
   // A mixed selection keeps the real control with "Mixed" as its placeholder
diff --git a/apps/web/src/components/ui/alert-dialog.tsx b/apps/web/src/components/ui/alert-dialog.tsx
index 6e6c1ce2b210..7cd6d40c59ee 100644
--- a/apps/web/src/components/ui/alert-dialog.tsx
+++ b/apps/web/src/components/ui/alert-dialog.tsx
@@ -101,7 +101,7 @@ function AlertDialogFooter({
 function AlertDialogTitle({ className, ...props }: AlertDialogPrimitive.Title.Props) {
   return (
     <AlertDialogPrimitive.Title
-      className={cn("font-heading font-semibold text-xl leading-none", className)}
+      className={cn("wrap-anywhere font-heading font-semibold text-xl leading-none", className)}
       data-slot="alert-dialog-title"
       {...props}
     />
diff --git a/apps/web/src/components/ui/dialog.tsx b/apps/web/src/components/ui/dialog.tsx
index 22ce5637204f..db1b6e35b80f 100644
--- a/apps/web/src/components/ui/dialog.tsx
+++ b/apps/web/src/components/ui/dialog.tsx
@@ -145,7 +145,7 @@ function DialogFooter({
 function DialogTitle({ className, ...props }: DialogPrimitive.Title.Props) {
   return (
     <DialogPrimitive.Title
-      className={cn("font-heading font-semibold text-xl leading-none", className)}
+      className={cn("wrap-anywhere font-heading font-semibold text-xl leading-none", className)}
       data-slot="dialog-title"
       {...props}
     />
diff --git a/apps/web/src/components/ui/tooltip.tsx b/apps/web/src/components/ui/tooltip.tsx
index c0aaea40ceae..7ba9e4c238c4 100644
--- a/apps/web/src/components/ui/tooltip.tsx
+++ b/apps/web/src/components/ui/tooltip.tsx
@@ -23,7 +23,8 @@ function TooltipPopup({
   align?: TooltipPrimitive.Positioner.Props["align"];
   side?: TooltipPrimitive.Positioner.Props["side"];
   sideOffset?: TooltipPrimitive.Positioner.Props["sideOffset"];
-  variant?: "default" | "glass";
+  /** `code` renders monospace content that breaks anywhere, for paths and commands. */
+  variant?: "default" | "glass" | "code";
   anchor?: TooltipPrimitive.Positioner.Props["anchor"];
 }) {
   return (
@@ -42,6 +43,10 @@ function TooltipPopup({
             variant === "glass"
               ? "dropdown-glass shadow-xl shadow-black/25 before:hidden"
               : "border bg-popover not-dark:bg-clip-padding shadow-md/5",
+            // One wrap width for prose; code dumps get more room and break anywhere.
+            variant === "code"
+              ? "max-w-120 wrap-anywhere text-left font-mono text-[11px] leading-relaxed"
+              : "max-w-80 wrap-anywhere whitespace-normal leading-snug",
             className,
           )}
           data-slot="tooltip-popup"
diff --git a/apps/web/src/components/usage/UsageLimits.tsx b/apps/web/src/components/usage/UsageLimits.tsx
index 6d30d49a7e4a..05c91739e251 100644
--- a/apps/web/src/components/usage/UsageLimits.tsx
+++ b/apps/web/src/components/usage/UsageLimits.tsx
@@ -127,7 +127,7 @@ function WindowBar({
           />
         ) : null}
       </TooltipTrigger>
-      <TooltipPopup side="top" className="max-w-72 text-xs">
+      <TooltipPopup side="top">
         <div className="flex flex-col gap-0.5">
           <span className="text-foreground">
             {remaining}% left{timeLeft !== null ? ` · ${timeLeft}% of the window left` : ""}
diff --git a/apps/web/src/routes/_chat.pull-requests.tsx b/apps/web/src/routes/_chat.pull-requests.tsx
index ce2bd238746a..1e540d64634b 100644
--- a/apps/web/src/routes/_chat.pull-requests.tsx
+++ b/apps/web/src/routes/_chat.pull-requests.tsx
@@ -2280,9 +2280,7 @@ function CompactFilterMenu<Value extends string>({
             ) : (
               <Tooltip key={option.value}>
                 <TooltipTrigger render={item} />
-                <TooltipPopup side="right" className="max-w-64 break-words">
-                  {option.unavailable}
-                </TooltipPopup>
+                <TooltipPopup side="right">{option.unavailable}</TooltipPopup>
               </Tooltip>
             );
           })}
diff --git a/scripts/lint-restyle-ceiling.ts b/scripts/lint-restyle-ceiling.ts
index db8a73b20326..a0743a167631 100644
--- a/scripts/lint-restyle-ceiling.ts
+++ b/scripts/lint-restyle-ceiling.ts
@@ -8,7 +8,7 @@ import * as NodeURL from "node:url";
 // components/ui exports are migrated to variants (see vite.config.ts). This gate keeps the
 // count from growing: CI fails when findings exceed the ceiling. Lower the ceiling when you
 // migrate a file, and delete this script when the rule becomes an error.
-export const RESTYLE_CEILING = 981;
+export const RESTYLE_CEILING = 921;
 
 const RULE = "shadcn(no-restyle)";