diff --git a/apps/web/src/components/sidebar/SidebarThreadRow.tsx b/apps/web/src/components/sidebar/SidebarThreadRow.tsx
index fa87252de1457..ee9502c73e0a2 100644
--- a/apps/web/src/components/sidebar/SidebarThreadRow.tsx
+++ b/apps/web/src/components/sidebar/SidebarThreadRow.tsx
@@ -1004,6 +1004,7 @@ const SidebarThreadRow = memo(function SidebarThreadRow(props: SidebarThreadRowP
     isActive: props.isActive,
   });
 
+  const titleDirection = textDirection(thread.title);
   const title = isRenaming ? (
     <ThreadRenameInput
       title={renamingTitle}
@@ -1038,9 +1039,15 @@ const SidebarThreadRow = memo(function SidebarThreadRow(props: SidebarThreadRowP
             ),
         isRegeneratingTitle && "opacity-55",
       )}
-      dir={textDirection(thread.title)}
+      dir={titleDirection}
     >
-      {thread.title}
+      {/* The measured cut assumes left-to-right text, so RTL titles keep their end ellipsis. */}
+      <MiddleTruncate
+        value={thread.title}
+        {...(titleDirection === "rtl" ? { tail: 0 } : {})}
+        showTitle={false}
+        className="flex"
+      />
     </span>
   );
   const accessibleTitle = isRenaming ? null : <span className="sr-only">{thread.title}</span>;
@@ -1736,7 +1743,13 @@ export const SidebarSearchResultRow = memo(function SidebarSearchResultRow(props
                   thread.titleRegeneration != null && "opacity-55",
                 )}
               >
-                {thread.title}
+                <MiddleTruncate
+                  value={thread.title}
+                  {...(textDirection(thread.title) === "rtl" ? { tail: 0 } : {})}
+                  dir={textDirection(thread.title)}
+                  showTitle={false}
+                  className="flex"
+                />
               </span>
               <span id={`${props.resultId}-pr`} className="contents">
                 <ThreadSearchPullRequestNumber
diff --git a/apps/web/src/components/ui/middle-truncate.test.ts b/apps/web/src/components/ui/middle-truncate.test.ts
index 5a83189265ebf..39be72d9100b9 100644
--- a/apps/web/src/components/ui/middle-truncate.test.ts
+++ b/apps/web/src/components/ui/middle-truncate.test.ts
@@ -23,6 +23,17 @@ describe("splitForMiddleTruncate", () => {
     expect(splitForMiddleTruncate("t3/abcdefghijklmnopqrstuvwxyz")?.tail).toBe("qrstuvwxyz");
   });
 
+  it("starts a title's tail on a word", () => {
+    expect(splitForMiddleTruncate("Debate Weaknesses in Bilateral Agreements")).toEqual({
+      head: "Debate Weaknesses in Bilateral ",
+      tail: "Agreements",
+    });
+  });
+
+  it("flattens line breaks so a value stays on one line", () => {
+    expect(splitForMiddleTruncate("first\nsecond line of a label")?.head).not.toContain("\n");
+  });
+
   it("respects an explicit tail length", () => {
     expect(splitForMiddleTruncate("t3/clone-repo-to-other-machine", 6)?.tail).toBe("achine");
   });
diff --git a/apps/web/src/components/ui/middle-truncate.tsx b/apps/web/src/components/ui/middle-truncate.tsx
index 62dd3c58ecce3..1315e4ac27f5c 100644
--- a/apps/web/src/components/ui/middle-truncate.tsx
+++ b/apps/web/src/components/ui/middle-truncate.tsx
@@ -19,19 +19,20 @@ export function MiddleTruncate({
   const split = splitForMiddleTruncate(value, tail);
   const headRef = useRef<HTMLSpanElement>(null);
   const head = split?.head;
+  const suffix = split?.tail;
   // oxlint-disable-next-line t3code/no-unreasoned-state-sync -- fits the head span's DOM text and refits it through a ResizeObserver
   useLayoutEffect(() => {
     const element = headRef.current;
     // A new head can keep the same box size, so refit here, not only on resize.
-    if (!element || head === undefined) return;
+    if (!element || !element.parentElement || head === undefined || suffix === undefined) return;
     fitHead(element);
-    return observeResize(element, () => fitHead(element));
-  }, [head]);
+    return observeResize([element, element.parentElement], () => fitHead(element));
+  }, [head, suffix]);
   return (
     <span
       {...(showTitle ? { title: value } : {})}
       className={cn(
-        "inline-flex min-w-0 max-w-full overflow-hidden whitespace-nowrap",
+        "group/middle-truncate relative inline-flex min-w-0 max-w-full overflow-hidden whitespace-nowrap",
         variant === "cap-aligned" &&
           // Padding keeps descenders inside the box, so the cut does not clip them.
           "overflow-x-clip overflow-y-visible [&>span]:[text-box:trim-both_cap_alphabetic] [&>span]:-mb-1 [&>span]:pb-1 [&>span]:overflow-x-clip [&>span]:overflow-y-visible",
@@ -42,10 +43,19 @@ export function MiddleTruncate({
       {split ? (
         <>
           {/* The tail carries the ellipsis so it sits flush; a CSS ellipsis leaves a ragged gap. */}
-          <span ref={headRef} className="peer min-w-0 overflow-hidden">
+          <span
+            ref={headRef}
+            className="peer min-w-0 overflow-hidden whitespace-pre group-data-tail-overflow/middle-truncate:invisible group-data-tail-overflow/middle-truncate:absolute"
+          >
             {split.head}
           </span>
-          <span className="shrink-0 peer-data-overflow:before:content-['…']">{split.tail}</span>
+          <span className="w-max shrink-0 whitespace-pre peer-data-overflow:before:content-['…'] group-data-tail-overflow/middle-truncate:invisible group-data-tail-overflow/middle-truncate:absolute">
+            {split.tail}
+          </span>
+          <span className="hidden min-w-0 truncate group-data-tail-overflow/middle-truncate:block">
+            {split.head}
+            {split.tail}
+          </span>
         </>
       ) : (
         // Keyed so React does not reuse the head node and its imperative clip.
@@ -62,9 +72,16 @@ export function MiddleTruncate({
 // size stays the true available width.
 
 function fitHead(head: HTMLElement) {
+  const container = head.parentElement;
+  const tail = head.nextElementSibling;
+  container?.removeAttribute("data-tail-overflow");
   const text = head.firstChild;
   const overflowing = head.scrollWidth > head.clientWidth && text instanceof Text;
   head.toggleAttribute("data-overflow", overflowing);
+  if (container && tail instanceof HTMLElement && tail.offsetWidth > container.clientWidth) {
+    container.setAttribute("data-tail-overflow", "");
+    return;
+  }
   let slack = 0;
   if (overflowing) {
     const range = document.createRange();
@@ -85,21 +102,20 @@ function fitHead(head: HTMLElement) {
     slack = Math.max(0, head.clientWidth - widthTo(fits));
   }
   head.style.clipPath = slack > 0 ? `inset(-0.25em ${slack}px -0.25em 0)` : "";
-  const tail = head.nextElementSibling;
   if (tail instanceof HTMLElement) tail.style.translate = slack > 0 ? `-${slack}px 0` : "";
 }
 
 const DEFAULT_TAIL = 10;
 const MAX_SEGMENT_TAIL = 16;
 const MIN_WORD_TAIL = 4;
-const WORD_BREAK = /[-_./]/;
+const WORD_BREAK = /[-_./\s]/;
 
 export function splitForMiddleTruncate(
   value: string,
   tail?: number,
 ): { head: string; tail: string } | null {
   // Split by code point to avoid cutting surrogate pairs into broken glyphs.
-  const chars = Array.from(value);
+  const chars = Array.from(value.replace(/[\r\n]+/g, " "));
   let keep = tail ?? DEFAULT_TAIL;
   if (tail === undefined) {
     const slash = chars.lastIndexOf("/");