diff --git a/extensions/discord/src/chunk.test.ts b/extensions/discord/src/chunk.test.ts
index 11b28749d24b..0e9c81d15434 100644
--- a/extensions/discord/src/chunk.test.ts
+++ b/extensions/discord/src/chunk.test.ts
@@ -78,6 +78,17 @@ describe("chunkDiscordText", () => {
     }
   });
 
+  it("keeps chunks within maxChars when a closing fence line carries trailing text", () => {
+    // A line that both closes the fence and carries a long tail must still reserve closing-fence
+    // space; otherwise a mid-line flush appended "```" and overflowed maxChars (e.g. 2004 > 2000).
+    for (let pad = 1990; pad <= 2000; pad++) {
+      const text = "hi\n```lang\n```" + "z".repeat(pad);
+      for (const chunk of chunkDiscordText(text, { maxChars: 2000, maxLines: 100 })) {
+        expect(chunk.length).toBeLessThanOrEqual(2000);
+      }
+    }
+  });
+
   it("preserves whitespace when splitting long lines", () => {
     const text = Array.from({ length: 40 }, () => "word").join(" ");
     const chunks = chunkDiscordText(text, { maxChars: 20, maxLines: 50 });
diff --git a/extensions/discord/src/chunk.ts b/extensions/discord/src/chunk.ts
index d78050605218..952dc150c6d3 100644
--- a/extensions/discord/src/chunk.ts
+++ b/extensions/discord/src/chunk.ts
@@ -207,8 +207,12 @@ export function chunkDiscordText(text: string, opts: ChunkDiscordTextOpts = {}):
       }
     }
 
-    const reserveChars = nextOpenFence ? closeFenceLine(nextOpenFence).length + 1 : 0;
-    const reserveLines = nextOpenFence ? 1 : 0;
+    // A flush can fire mid-line, before `openFence` advances to `nextOpenFence` below, so it closes
+    // against the still-open `openFence`. A fence-closing line that also carries trailing text would
+    // otherwise reserve 0 yet still get a closing fence appended on flush, overflowing maxChars.
+    const fenceToReserve = nextOpenFence ?? openFence;
+    const reserveChars = fenceToReserve ? closeFenceLine(fenceToReserve).length + 1 : 0;
+    const reserveLines = fenceToReserve ? 1 : 0;
     const effectiveMaxChars = maxChars - reserveChars;
     const effectiveMaxLines = maxLines - reserveLines;
     const charLimit = effectiveMaxChars > 0 ? effectiveMaxChars : maxChars;