diff --git a/packages/cli-v3/src/utilities/windows.test.ts b/packages/cli-v3/src/utilities/windows.test.ts
new file mode 100644
index 00000000000..425d69cfa8b
--- /dev/null
+++ b/packages/cli-v3/src/utilities/windows.test.ts
@@ -0,0 +1,69 @@
+import { afterEach, describe, expect, it } from "vitest";
+import { truncateMessage } from "./windows.js";
+
+const originalIsTTY = process.stdout.isTTY;
+const originalColumns = process.stdout.columns;
+
+function mockStdout(options: { isTTY: boolean; columns?: number | undefined }) {
+  Object.defineProperty(process.stdout, "isTTY", {
+    configurable: true,
+    value: options.isTTY,
+  });
+
+  Object.defineProperty(process.stdout, "columns", {
+    configurable: true,
+    value: options.columns,
+  });
+}
+
+afterEach(() => {
+  Object.defineProperty(process.stdout, "isTTY", {
+    configurable: true,
+    value: originalIsTTY,
+  });
+
+  Object.defineProperty(process.stdout, "columns", {
+    configurable: true,
+    value: originalColumns,
+  });
+});
+
+describe("truncateMessage", () => {
+  it("returns the original message when stdout is not a TTY", () => {
+    mockStdout({ isTTY: false, columns: undefined });
+
+    const message = "a".repeat(500);
+
+    expect(truncateMessage(message)).toBe(message);
+  });
+
+  it("returns the original message when stdout has no columns", () => {
+    mockStdout({ isTTY: true, columns: undefined });
+
+    const message = "a".repeat(500);
+
+    expect(truncateMessage(message)).toBe(message);
+  });
+
+  it("does not truncate short messages", () => {
+    expect(truncateMessage("hello", 20)).toBe("hello");
+  });
+
+  it("truncates long plain messages", () => {
+    expect(truncateMessage("hello world", 12)).toBe("hell...");
+  });
+
+  it("truncates ANSI-colored messages without counting escape codes", () => {
+    const message = "\x1b[31mhello world\x1b[39m";
+
+    expect(truncateMessage(message, 12)).toBe("\x1b[31mhell\x1b[0m...");
+  });
+
+  it("preserves terminal hyperlink escapes when truncating", () => {
+    const open = "\u001b]8;;https://trigger.dev\u0007";
+    const close = "\u001b]8;;\u0007";
+    const message = `${open}hello world${close}`;
+
+    expect(truncateMessage(message, 12)).toBe(`${open}hell${close}...`);
+  });
+});
diff --git a/packages/cli-v3/src/utilities/windows.ts b/packages/cli-v3/src/utilities/windows.ts
index 3ebf403f43b..dc9b982a0a1 100644
--- a/packages/cli-v3/src/utilities/windows.ts
+++ b/packages/cli-v3/src/utilities/windows.ts
@@ -7,18 +7,56 @@ export function escapeImportPath(path: string) {
   return isWindows ? path.replaceAll("\\", "\\\\") : path;
 }
 
+const terminalHyperlinkPattern = /\u001b]8;;[^\u0007]*\u0007/y;
+const ansiEscapePattern = /\x1b\[[0-9;]*[a-zA-Z]/y;
+const terminalHyperlinkClose = "\u001b]8;;\u0007";
+const ansiReset = "\u001b[0m";
+const ansiResetCodes = new Set([0, 22, 23, 24, 25, 27, 28, 29, 39, 49, 54, 55, 59]);
+
+function updateAnsiState(sequence: string, hasActiveSgr: boolean): boolean {
+  if (!sequence.endsWith("m")) {
+    return hasActiveSgr;
+  }
+
+  const rawCodes = sequence.slice(2, -1);
+  const codes = rawCodes === "" ? [0] : rawCodes.split(";").map(Number);
+
+  return codes.some((code) => !ansiResetCodes.has(code));
+}
+
 // Removes ANSI escape sequences to get actual visible length
 function getVisibleLength(str: string): number {
-  return (
-    str
-      // Remove terminal hyperlinks: \u001b]8;;URL\u0007TEXT\u001b]8;;\u0007
-      .replace(/\u001b]8;;[^\u0007]*\u0007/g, "")
-      // Remove standard ANSI escape sequences (colors, cursor movement, etc.)
-      .replace(/\x1b\[[0-9;]*[a-zA-Z]/g, "").length
-  );
+  let visibleLength = 0;
+
+  for (let index = 0; index < str.length; ) {
+    terminalHyperlinkPattern.lastIndex = index;
+    const terminalHyperlinkMatch = terminalHyperlinkPattern.exec(str);
+
+    if (terminalHyperlinkMatch) {
+      index += terminalHyperlinkMatch[0].length;
+      continue;
+    }
+
+    ansiEscapePattern.lastIndex = index;
+    const ansiEscapeMatch = ansiEscapePattern.exec(str);
+
+    if (ansiEscapeMatch) {
+      index += ansiEscapeMatch[0].length;
+      continue;
+    }
+
+    visibleLength += 1;
+    index += 1;
+  }
+
+  return visibleLength;
 }
 
-function truncateMessage(msg: string, maxLength?: number): string {
+export function truncateMessage(msg: string, maxLength?: number): string {
+  if (maxLength === undefined && (!process.stdout.isTTY || process.stdout.columns == null)) {
+    return msg;
+  }
+
   const terminalWidth = maxLength ?? process.stdout.columns ?? 80;
   const availableWidth = terminalWidth - 5; // Reserve some space for the spinner and padding
   const visibleLength = getVisibleLength(msg);
@@ -27,11 +65,76 @@ function truncateMessage(msg: string, maxLength?: number): string {
     return msg;
   }
 
+  const maxVisibleLength = availableWidth - 3;
+
   // We need to truncate based on visible characters, but preserve ANSI sequences
-  // Simple approach: truncate character by character until we fit
-  let truncated = msg;
-  while (getVisibleLength(truncated) > availableWidth - 3) {
-    truncated = truncated.slice(0, -1);
+  let truncated = "";
+  let truncatedVisibleLength = 0;
+  let hasActiveSgr = false;
+  let hasActiveHyperlink = false;
+
+  for (let index = 0; index < msg.length && truncatedVisibleLength < maxVisibleLength; ) {
+    terminalHyperlinkPattern.lastIndex = index;
+    const terminalHyperlinkMatch = terminalHyperlinkPattern.exec(msg);
+
+    if (terminalHyperlinkMatch) {
+      const sequence = terminalHyperlinkMatch[0];
+      truncated += sequence;
+      hasActiveHyperlink = sequence !== terminalHyperlinkClose;
+      index += sequence.length;
+      continue;
+    }
+
+    ansiEscapePattern.lastIndex = index;
+    const ansiEscapeMatch = ansiEscapePattern.exec(msg);
+
+    if (ansiEscapeMatch) {
+      const sequence = ansiEscapeMatch[0];
+      truncated += sequence;
+      hasActiveSgr = updateAnsiState(sequence, hasActiveSgr);
+      index += sequence.length;
+      continue;
+    }
+
+    truncated += msg[index];
+    truncatedVisibleLength += 1;
+    index += 1;
+
+    if (truncatedVisibleLength === maxVisibleLength) {
+      while (index < msg.length) {
+        terminalHyperlinkPattern.lastIndex = index;
+        const trailingTerminalHyperlinkMatch = terminalHyperlinkPattern.exec(msg);
+
+        if (trailingTerminalHyperlinkMatch) {
+          const sequence = trailingTerminalHyperlinkMatch[0];
+          truncated += sequence;
+          hasActiveHyperlink = sequence !== terminalHyperlinkClose;
+          index += sequence.length;
+          continue;
+        }
+
+        ansiEscapePattern.lastIndex = index;
+        const trailingAnsiEscapeMatch = ansiEscapePattern.exec(msg);
+
+        if (trailingAnsiEscapeMatch) {
+          const sequence = trailingAnsiEscapeMatch[0];
+          truncated += sequence;
+          hasActiveSgr = updateAnsiState(sequence, hasActiveSgr);
+          index += sequence.length;
+          continue;
+        }
+
+        break;
+      }
+    }
+  }
+
+  if (hasActiveHyperlink) {
+    truncated += terminalHyperlinkClose;
+  }
+
+  if (hasActiveSgr) {
+    truncated += ansiReset;
   }
 
   return truncated + "...";