From d2649e041067f4b2d19e68d6896cf6a24d901e32 Mon Sep 17 00:00:00 2001
From: evgyur <evgyur@example.com>
Date: Mon, 4 May 2026 02:31:29 +0300
Subject: [PATCH] fix(telegram): preserve spacing before numbered sections

---
 extensions/telegram/src/format.test.ts | 27 ++++++++++++++++
 extensions/telegram/src/format.ts      | 43 ++++++++++++++++++++++++--
 2 files changed, 68 insertions(+), 2 deletions(-)

diff --git a/extensions/telegram/src/format.test.ts b/extensions/telegram/src/format.test.ts
index 2fcd06663e0..70f09cab856 100644
--- a/extensions/telegram/src/format.test.ts
+++ b/extensions/telegram/src/format.test.ts
@@ -95,6 +95,33 @@ describe("markdownToTelegramHtml", () => {
     expect(res).toBe("<tg-spoiler><b>secret</b> text</tg-spoiler>");
   });
 
+  it("preserves spacing between Telegram bullet blocks and following numbered sections", () => {
+    const input = [
+      "2. Main invariants:",
+      "",
+      "  • Raw Log is source of truth.",
+      "  • Autonomy starts only with report/draft.",
+      "3. Cognee is a candidate:",
+      "",
+      "  • bake-off first;",
+      "  • decide keep/adopt/hybrid later.",
+      "4. Project Flow slices:",
+    ].join("\n");
+
+    const res = markdownToTelegramHtml(input, { wrapFileRefs: false });
+
+    expect(res).toContain("report/draft.\n\n3. Cognee");
+    expect(res).toContain("keep/adopt/hybrid later.\n\n4. Project");
+  });
+
+  it("does not insert Telegram list boundary spacing inside fenced code", () => {
+    const input = ["```", "  • literal bullet", "3. literal number", "```"].join("\n");
+
+    const res = markdownToTelegramHtml(input, { wrapFileRefs: false });
+
+    expect(res).toBe("<pre><code>  • literal bullet\n3. literal number\n</code></pre>");
+  });
+
   it("does not treat single pipe as spoiler", () => {
     const res = markdownToTelegramHtml("(￣_￣|) face");
     expect(res).not.toContain("tg-spoiler");
diff --git a/extensions/telegram/src/format.ts b/extensions/telegram/src/format.ts
index 080af504b15..c959903c475 100644
--- a/extensions/telegram/src/format.ts
+++ b/extensions/telegram/src/format.ts
@@ -72,11 +72,50 @@ function renderTelegramHtml(ir: MarkdownIR): string {
   });
 }
 
+function leadingWhitespaceLength(line: string): number {
+  return line.match(/^[ \t]*/)?.[0]?.length ?? 0;
+}
+
+function isTelegramBulletLine(line: string): boolean {
+  return /^[ \t]*(?:[•*+-])[ \t]+\S/.test(line);
+}
+
+function isTelegramListBoundaryLine(line: string): boolean {
+  return /^[ \t]*(?:\d+\.|#{1,6})[ \t]+\S/.test(line);
+}
+
+function preserveTelegramListBoundarySpacing(markdown: string): string {
+  const lines = markdown.split("\n");
+  const out: string[] = [];
+  let inFence = false;
+
+  for (const line of lines) {
+    const normalizedLine = line.replace(/\r$/, "");
+    const isFenceLine = /^[ \t]*(?:```|~~~)/.test(normalizedLine);
+    if (!inFence && out.length > 0) {
+      const previous = out[out.length - 1] ?? "";
+      if (
+        isTelegramBulletLine(previous) &&
+        isTelegramListBoundaryLine(normalizedLine) &&
+        leadingWhitespaceLength(normalizedLine) <= leadingWhitespaceLength(previous)
+      ) {
+        out.push("");
+      }
+    }
+    out.push(line);
+    if (isFenceLine) {
+      inFence = !inFence;
+    }
+  }
+
+  return out.join("\n");
+}
+
 export function markdownToTelegramHtml(
   markdown: string,
   options: { tableMode?: MarkdownTableMode; wrapFileRefs?: boolean } = {},
 ): string {
-  const ir = markdownToIR(markdown ?? "", {
+  const ir = markdownToIR(preserveTelegramListBoundarySpacing(markdown ?? ""), {
     linkify: true,
     enableSpoilers: true,
     headingStyle: "none",
@@ -458,7 +497,7 @@ export function markdownToTelegramChunks(
   limit: number,
   options: { tableMode?: MarkdownTableMode } = {},
 ): TelegramFormattedChunk[] {
-  const ir = markdownToIR(markdown ?? "", {
+  const ir = markdownToIR(preserveTelegramListBoundarySpacing(markdown ?? ""), {
     linkify: true,
     enableSpoilers: true,
     headingStyle: "none",