diff --git a/packages/ui/src/features/canvas/components/ChannelFeedView.test.tsx b/packages/ui/src/features/canvas/components/ChannelFeedView.test.tsx
index 6e43636df6..fd7842441b 100644
--- a/packages/ui/src/features/canvas/components/ChannelFeedView.test.tsx
+++ b/packages/ui/src/features/canvas/components/ChannelFeedView.test.tsx
@@ -2,7 +2,7 @@ import type { Task } from "@posthog/shared/domain-types";
 import { Theme } from "@radix-ui/themes";
 import { render, screen } from "@testing-library/react";
 import userEvent from "@testing-library/user-event";
-import { describe, expect, it, vi } from "vitest";
+import { afterEach, describe, expect, it, vi } from "vitest";
 import { TaskFeedRow } from "./ChannelFeedView";
 
 const task = {
@@ -24,22 +24,60 @@ const task = {
 } satisfies Task;
 
 describe("TaskFeedRow", () => {
+  afterEach(() => {
+    vi.restoreAllMocks();
+  });
+
   it("expands a truncated prompt", async () => {
-    vi.spyOn(HTMLElement.prototype, "scrollHeight", "get").mockReturnValue(60);
+    vi.spyOn(HTMLElement.prototype, "scrollHeight", "get").mockImplementation(
+      function (this: HTMLElement) {
+        return (this.textContent?.length ?? 0) > 35 ? 60 : 20;
+      },
+    );
     vi.spyOn(HTMLElement.prototype, "clientHeight", "get").mockReturnValue(40);
     const user = userEvent.setup();
-    render(
+    const { container } = render(
       <Theme>
         <TaskFeedRow task={task} />
       </Theme>,
     );
 
-    const prompt = screen.getByText(task.description);
-    expect(prompt).toHaveClass("line-clamp-2");
+    const prompt = container.querySelector(
+      '[data-slot="thread-item-body"]:not([aria-hidden])',
+    );
+    const more = screen.getByRole("button", { name: "more" });
+    expect(prompt).toHaveTextContent(/\.\.\. more$/);
+    expect(prompt).toContainElement(more);
 
-    await user.click(screen.getByRole("button", { name: "more" }));
+    await user.click(more);
 
-    expect(prompt).not.toHaveClass("line-clamp-2");
+    expect(prompt).toHaveTextContent(task.description);
     expect(screen.getByRole("button", { name: "less" })).toBeInTheDocument();
   });
+
+  it("collapses newlines and whitespace before truncating", () => {
+    vi.spyOn(HTMLElement.prototype, "scrollHeight", "get").mockImplementation(
+      function (this: HTMLElement) {
+        return (this.textContent?.length ?? 0) > 35 ? 60 : 20;
+      },
+    );
+    vi.spyOn(HTMLElement.prototype, "clientHeight", "get").mockReturnValue(40);
+    const multilineTask = {
+      ...task,
+      description:
+        "truncation was recently added to message prompts, but\n\nthere is more text after it",
+    };
+
+    const { container } = render(
+      <Theme>
+        <TaskFeedRow task={multilineTask} />
+      </Theme>,
+    );
+
+    const prompt = container.querySelector(
+      '[data-slot="thread-item-body"]:not([aria-hidden])',
+    );
+    expect(prompt?.textContent).not.toContain("\n");
+    expect(prompt).toHaveTextContent(/[^ ]\.\.\. more$/);
+  });
 });
diff --git a/packages/ui/src/features/canvas/components/ChannelFeedView.tsx b/packages/ui/src/features/canvas/components/ChannelFeedView.tsx
index 026026b0a9..7a2662024f 100644
--- a/packages/ui/src/features/canvas/components/ChannelFeedView.tsx
+++ b/packages/ui/src/features/canvas/components/ChannelFeedView.tsx
@@ -422,42 +422,80 @@ function ExpandablePrompt({
 }) {
   const observerRef = useRef<ResizeObserver | null>(null);
   const [expanded, setExpanded] = useState(false);
-  const [truncated, setTruncated] = useState(false);
+  const [truncatedText, setTruncatedText] = useState<string | null>(null);
+  const measureTextRef = useRef<HTMLSpanElement>(null);
+  const measureMoreRef = useRef<HTMLSpanElement>(null);
+  const collapsedText = children.replace(/\s+/g, " ").trim();
 
   const measureRef = useCallback(
     (body: HTMLDivElement | null) => {
       observerRef.current?.disconnect();
       observerRef.current = null;
       if (!body || expanded) return;
-      const measure = () => setTruncated(body.scrollHeight > body.clientHeight);
+      const measure = () => {
+        const text = measureTextRef.current;
+        const more = measureMoreRef.current;
+        if (!text || !more) return;
+
+        more.hidden = true;
+        text.textContent = collapsedText;
+        if (body.scrollHeight <= body.clientHeight) {
+          setTruncatedText(null);
+          return;
+        }
+
+        more.hidden = false;
+        let low = 0;
+        let high = collapsedText.length;
+        while (low < high) {
+          const middle = Math.ceil((low + high) / 2);
+          text.textContent = `${collapsedText.slice(0, middle).trimEnd()}... `;
+          if (body.scrollHeight <= body.clientHeight) {
+            low = middle;
+          } else {
+            high = middle - 1;
+          }
+        }
+        setTruncatedText(collapsedText.slice(0, low).trimEnd());
+      };
       measure();
       const observer = new ResizeObserver(measure);
-      observer.observe(body);
+      observer.observe(body.parentElement ?? body);
       observerRef.current = observer;
     },
-    [expanded],
+    [collapsedText, expanded],
   );
 
   return (
-    <div>
-      <ThreadItemBody
-        ref={measureRef}
-        className={cn(
-          "wrap-break-word whitespace-pre-wrap",
-          !expanded && (lines === 2 ? "line-clamp-2" : "line-clamp-4"),
+    <div className="relative">
+      <ThreadItemBody className="wrap-break-word whitespace-pre-wrap">
+        {expanded || truncatedText === null ? children : truncatedText}
+        {truncatedText !== null && !expanded && "... "}
+        {truncatedText !== null && (
+          <button
+            type="button"
+            aria-expanded={expanded}
+            className="text-muted-foreground text-xs underline underline-offset-2 hover:text-foreground"
+            onClick={() => setExpanded((value) => !value)}
+          >
+            {expanded ? "less" : "more"}
+          </button>
         )}
-      >
-        {children}
       </ThreadItemBody>
-      {(truncated || expanded) && (
-        <button
-          type="button"
-          aria-expanded={expanded}
-          className="text-muted-foreground text-xs underline underline-offset-2 hover:text-foreground"
-          onClick={() => setExpanded((value) => !value)}
+      {!expanded && (
+        <ThreadItemBody
+          ref={measureRef}
+          aria-hidden="true"
+          className={cn(
+            "wrap-break-word pointer-events-none invisible absolute inset-x-0 top-0 whitespace-normal",
+            lines === 2 ? "line-clamp-2" : "line-clamp-4",
+          )}
         >
-          {expanded ? "less" : "more"}
-        </button>
+          <span ref={measureTextRef}>{collapsedText}</span>
+          <span ref={measureMoreRef} className="text-xs">
+            more
+          </span>
+        </ThreadItemBody>
       )}
     </div>
   );