From ef9a5f9889582e08467b01cead41aaafd70d220a Mon Sep 17 00:00:00 2001
From: harjoth <harjoth.khara@gmail.com>
Date: Fri, 10 Jul 2026 18:16:05 -0700
Subject: [PATCH] fix(desktop): preserve matched URL parentheses

(cherry picked from commit 6e126d8575859f9ca7a6d20240e2e2ba61c74b7b)
---
 .../assistant-ui/markdown-text.test.ts        | 18 ++++++++++
 apps/desktop/src/lib/markdown-preprocess.ts   | 35 ++++++++++---------
 2 files changed, 37 insertions(+), 16 deletions(-)

diff --git a/apps/desktop/src/components/assistant-ui/markdown-text.test.ts b/apps/desktop/src/components/assistant-ui/markdown-text.test.ts
index 5914bb7a09..413a2e2459 100644
--- a/apps/desktop/src/components/assistant-ui/markdown-text.test.ts
+++ b/apps/desktop/src/components/assistant-ui/markdown-text.test.ts
@@ -134,6 +134,24 @@ describe('preprocessMarkdown', () => {
     expect(output).toContain('<https://example.com/wiki/Foo_(bar)>')
   })
 
+  it('preserves a trailing balanced pair after an earlier stray closing paren', () => {
+    const output = preprocessMarkdown('See https://example.com/a)(b)')
+
+    expect(output).toContain('<https://example.com/a)(b)>')
+  })
+
+  it('strips three wrapper closing parens from raw-url autolinks', () => {
+    const output = preprocessMarkdown('(((https://example.com/page)))')
+
+    expect(output).toBe('(((<https://example.com/page>)))')
+  })
+
+  it('preserves an unmatched opening paren at the end of a raw URL', () => {
+    const output = preprocessMarkdown('https://example.com/foo(')
+
+    expect(output).toContain('<https://example.com/foo(>')
+  })
+
   it('strips only the wrapper closing paren around balanced-paren URLs', () => {
     const output = preprocessMarkdown('(https://example.com/wiki/Foo_(bar))')
 
diff --git a/apps/desktop/src/lib/markdown-preprocess.ts b/apps/desktop/src/lib/markdown-preprocess.ts
index eb606f9c29..59ee564702 100644
--- a/apps/desktop/src/lib/markdown-preprocess.ts
+++ b/apps/desktop/src/lib/markdown-preprocess.ts
@@ -211,29 +211,32 @@ function isUrlOnlyBlock(lines: string[]): boolean {
 // Strip only the *unbalanced* trailing `)` — the closing paren of a prose
 // wrapper like `(https://example.com/page)`, which the bare-URL matcher
 // greedily captures into the href. Parens that belong to the URL itself
-// (`…/wiki/Foo_(bar)`) stay intact: a trailing `)` is peeled only while the
-// URL holds more `)` than `(`. Count once, then trim from the end — the loop
-// only ever removes trailing closers, so `opens` never changes.
+// (`…/wiki/Foo_(bar)`) stay intact. Track normal left-to-right pairing and
+// peel only a suffix made entirely of unmatched closing parens; this avoids
+// sacrificing a valid trailing pair when an earlier stray `)` exists.
 function trimUnbalancedTrailingParens(url: string): string {
-  let opens = 0
-  let closes = 0
+  let depth = 0
+  let unmatchedSuffixStart: number | null = null
+
+  for (let index = 0; index < url.length; index += 1) {
+    const char = url[index]
 
-  for (const char of url) {
     if (char === '(') {
-      opens += 1
+      depth += 1
+      unmatchedSuffixStart = null
     } else if (char === ')') {
-      closes += 1
+      if (depth > 0) {
+        depth -= 1
+        unmatchedSuffixStart = null
+      } else if (unmatchedSuffixStart === null) {
+        unmatchedSuffixStart = index
+      }
+    } else {
+      unmatchedSuffixStart = null
     }
   }
 
-  let end = url.length
-
-  while (closes > opens && url[end - 1] === ')') {
-    closes -= 1
-    end -= 1
-  }
-
-  return url.slice(0, end)
+  return unmatchedSuffixStart === null ? url : url.slice(0, unmatchedSuffixStart)
 }
 
 function autoLinkRawUrls(text: string): string {