diff --git a/src/markdown/ir.blockquote-spacing.test.ts b/src/markdown/ir.blockquote-spacing.test.ts
new file mode 100644
index 00000000000..635b1f8e807
--- /dev/null
+++ b/src/markdown/ir.blockquote-spacing.test.ts
@@ -0,0 +1,202 @@
+/**
+ * Blockquote Spacing Tests
+ *
+ * Per CommonMark spec (§5.1 Block quotes), blockquotes are "container blocks" that
+ * contain other block-level elements (paragraphs, code blocks, etc.).
+ *
+ * In plaintext rendering, the expected spacing between block-level elements is
+ * a single blank line (double newline `\n\n`). This is the standard paragraph
+ * separation used throughout markdown.
+ *
+ * CORRECT behavior:
+ *   - Blockquote content followed by paragraph: "quote\n\nparagraph" (double \n)
+ *   - Two consecutive blockquotes: "first\n\nsecond" (double \n)
+ *
+ * BUG (current behavior):
+ *   - Produces triple newlines: "quote\n\n\nparagraph"
+ *
+ * Root cause:
+ *   1. `paragraph_close` inside blockquote adds `\n\n` (correct)
+ *   2. `blockquote_close` adds another `\n` (incorrect)
+ *   3. Result: `\n\n\n` (triple newlines - incorrect)
+ *
+ * The fix: `blockquote_close` should NOT add `\n` because:
+ *   - Blockquotes are container blocks, not leaf blocks
+ *   - The inner content (paragraph, heading, etc.) already provides block separation
+ *   - Container closings shouldn't add their own spacing
+ */
+
+import { describe, it, expect } from "vitest";
+import { markdownToIR } from "./ir.js";
+
+describe("blockquote spacing", () => {
+  describe("blockquote followed by paragraph", () => {
+    it("should have double newline (one blank line) between blockquote and paragraph", () => {
+      const input = "> quote\n\nparagraph";
+      const result = markdownToIR(input);
+
+      // CORRECT: "quote\n\nparagraph" (double newline)
+      // BUG: "quote\n\n\nparagraph" (triple newline)
+      expect(result.text).toBe("quote\n\nparagraph");
+    });
+
+    it("should not produce triple newlines", () => {
+      const input = "> quote\n\nparagraph";
+      const result = markdownToIR(input);
+
+      expect(result.text).not.toContain("\n\n\n");
+    });
+  });
+
+  describe("consecutive blockquotes", () => {
+    it("should have double newline between two blockquotes", () => {
+      const input = "> first\n\n> second";
+      const result = markdownToIR(input);
+
+      expect(result.text).toBe("first\n\nsecond");
+    });
+
+    it("should not produce triple newlines between blockquotes", () => {
+      const input = "> first\n\n> second";
+      const result = markdownToIR(input);
+
+      expect(result.text).not.toContain("\n\n\n");
+    });
+  });
+
+  describe("nested blockquotes", () => {
+    it("should handle nested blockquotes correctly", () => {
+      const input = "> outer\n>> inner";
+      const result = markdownToIR(input);
+
+      // Inner blockquote becomes separate paragraph
+      expect(result.text).toBe("outer\n\ninner");
+    });
+
+    it("should not produce triple newlines in nested blockquotes", () => {
+      const input = "> outer\n>> inner\n\nparagraph";
+      const result = markdownToIR(input);
+
+      expect(result.text).not.toContain("\n\n\n");
+    });
+
+    it("should handle deeply nested blockquotes", () => {
+      const input = "> level 1\n>> level 2\n>>> level 3";
+      const result = markdownToIR(input);
+
+      // Each nested level is a new paragraph
+      expect(result.text).not.toContain("\n\n\n");
+    });
+  });
+
+  describe("blockquote followed by other block elements", () => {
+    it("should have double newline between blockquote and heading", () => {
+      const input = "> quote\n\n# Heading";
+      const result = markdownToIR(input);
+
+      expect(result.text).toBe("quote\n\nHeading");
+      expect(result.text).not.toContain("\n\n\n");
+    });
+
+    it("should have double newline between blockquote and list", () => {
+      const input = "> quote\n\n- item";
+      const result = markdownToIR(input);
+
+      // The list item becomes "• item"
+      expect(result.text).toBe("quote\n\n• item");
+      expect(result.text).not.toContain("\n\n\n");
+    });
+
+    it("should have double newline between blockquote and code block", () => {
+      const input = "> quote\n\n```\ncode\n```";
+      const result = markdownToIR(input);
+
+      // Code blocks preserve their trailing newline
+      expect(result.text.startsWith("quote\n\ncode")).toBe(true);
+      expect(result.text).not.toContain("\n\n\n");
+    });
+
+    it("should have double newline between blockquote and horizontal rule", () => {
+      const input = "> quote\n\n---\n\nparagraph";
+      const result = markdownToIR(input);
+
+      // HR just adds a newline in IR, but should not create triple newlines
+      expect(result.text).not.toContain("\n\n\n");
+    });
+  });
+
+  describe("blockquote with multi-paragraph content", () => {
+    it("should handle multi-paragraph blockquote followed by paragraph", () => {
+      const input = "> first paragraph\n>\n> second paragraph\n\nfollowing paragraph";
+      const result = markdownToIR(input);
+
+      // Multi-paragraph blockquote should have proper internal spacing
+      // AND proper spacing with following content
+      expect(result.text).toContain("first paragraph\n\nsecond paragraph");
+      expect(result.text).not.toContain("\n\n\n");
+    });
+  });
+
+  describe("blockquote prefix option", () => {
+    it("should include prefix and maintain proper spacing", () => {
+      const input = "> quote\n\nparagraph";
+      const result = markdownToIR(input, { blockquotePrefix: "> " });
+
+      // With prefix, should still have proper spacing
+      expect(result.text).toBe("> quote\n\nparagraph");
+      expect(result.text).not.toContain("\n\n\n");
+    });
+  });
+
+  describe("edge cases", () => {
+    it("should handle empty blockquote followed by paragraph", () => {
+      const input = ">\n\nparagraph";
+      const result = markdownToIR(input);
+
+      expect(result.text).not.toContain("\n\n\n");
+    });
+
+    it("should handle blockquote at end of document", () => {
+      const input = "paragraph\n\n> quote";
+      const result = markdownToIR(input);
+
+      // No trailing triple newlines
+      expect(result.text).not.toContain("\n\n\n");
+    });
+
+    it("should handle multiple blockquotes with paragraphs between", () => {
+      const input = "> first\n\nparagraph\n\n> second";
+      const result = markdownToIR(input);
+
+      expect(result.text).toBe("first\n\nparagraph\n\nsecond");
+      expect(result.text).not.toContain("\n\n\n");
+    });
+  });
+});
+
+describe("comparison with other block elements (control group)", () => {
+  it("paragraphs should have double newline separation", () => {
+    const input = "paragraph 1\n\nparagraph 2";
+    const result = markdownToIR(input);
+
+    expect(result.text).toBe("paragraph 1\n\nparagraph 2");
+    expect(result.text).not.toContain("\n\n\n");
+  });
+
+  it("list followed by paragraph should have double newline", () => {
+    const input = "- item 1\n- item 2\n\nparagraph";
+    const result = markdownToIR(input);
+
+    // Lists already work correctly
+    expect(result.text).toContain("• item 2\n\nparagraph");
+    expect(result.text).not.toContain("\n\n\n");
+  });
+
+  it("heading followed by paragraph should have double newline", () => {
+    const input = "# Heading\n\nparagraph";
+    const result = markdownToIR(input);
+
+    expect(result.text).toBe("Heading\n\nparagraph");
+    expect(result.text).not.toContain("\n\n\n");
+  });
+});
diff --git a/src/markdown/ir.hr-spacing.test.ts b/src/markdown/ir.hr-spacing.test.ts
new file mode 100644
index 00000000000..c5bb6127bad
--- /dev/null
+++ b/src/markdown/ir.hr-spacing.test.ts
@@ -0,0 +1,173 @@
+import { describe, it, expect } from "vitest";
+import { markdownToIR } from "./ir.js";
+
+/**
+ * HR (Thematic Break) Spacing Analysis
+ * =====================================
+ *
+ * CommonMark Spec (0.31.2) Section 4.1 - Thematic Breaks:
+ * - Thematic breaks (---, ***, ___) produce <hr /> in HTML
+ * - "Thematic breaks do not need blank lines before or after"
+ * - A thematic break can interrupt a paragraph
+ *
+ * HTML Output per spec:
+ *   Input: "Foo\n***\nbar"
+ *   HTML:  "<p>Foo</p>\n<hr />\n<p>bar</p>"
+ *
+ * PLAIN TEXT OUTPUT DECISION:
+ *
+ * The HR element is a block-level thematic separator. In plain text output,
+ * we render HRs as a visible separator "───" to maintain visual distinction.
+ */
+
+describe("hr (thematic break) spacing", () => {
+  describe("current behavior documentation", () => {
+    it("just hr alone renders as separator", () => {
+      const result = markdownToIR("---");
+      expect(result.text).toBe("───");
+    });
+
+    it("hr between paragraphs renders with separator", () => {
+      const input = `Para 1
+
+---
+
+Para 2`;
+      const result = markdownToIR(input);
+      expect(result.text).toBe("Para 1\n\n───\n\nPara 2");
+    });
+
+    it("hr interrupting paragraph (setext heading case)", () => {
+      // Note: "Para\n---" is a setext heading in CommonMark!
+      // Using *** to test actual HR behavior
+      const input = `Para 1
+***
+Para 2`;
+      const result = markdownToIR(input);
+      // HR interrupts para, renders visibly
+      expect(result.text).toContain("───");
+    });
+  });
+
+  describe("expected behavior (tests assert CORRECT behavior)", () => {
+    it("hr between paragraphs should render with separator", () => {
+      const input = `Para 1
+
+---
+
+Para 2`;
+      const result = markdownToIR(input);
+      expect(result.text).toBe("Para 1\n\n───\n\nPara 2");
+    });
+
+    it("hr between paragraphs using *** should render with separator", () => {
+      const input = `Para 1
+
+***
+
+Para 2`;
+      const result = markdownToIR(input);
+      expect(result.text).toBe("Para 1\n\n───\n\nPara 2");
+    });
+
+    it("hr between paragraphs using ___ should render with separator", () => {
+      const input = `Para 1
+
+___
+
+Para 2`;
+      const result = markdownToIR(input);
+      expect(result.text).toBe("Para 1\n\n───\n\nPara 2");
+    });
+
+    it("consecutive hrs should produce multiple separators", () => {
+      const input = `---
+---
+---`;
+      const result = markdownToIR(input);
+      // Each HR renders as a separator
+      expect(result.text).toBe("───\n\n───\n\n───");
+    });
+
+    it("hr at document end renders separator", () => {
+      const input = `Para
+
+---`;
+      const result = markdownToIR(input);
+      expect(result.text).toBe("Para\n\n───");
+    });
+
+    it("hr at document start renders separator", () => {
+      const input = `---
+
+Para`;
+      const result = markdownToIR(input);
+      expect(result.text).toBe("───\n\nPara");
+    });
+
+    it("should not produce triple newlines regardless of hr placement", () => {
+      const inputs = [
+        "Para 1\n\n---\n\nPara 2",
+        "Para 1\n---\nPara 2",
+        "---\nPara",
+        "Para\n---",
+        "Para 1\n\n---\n\n---\n\nPara 2",
+        "Para 1\n\n***\n\n---\n\n___\n\nPara 2",
+      ];
+
+      for (const input of inputs) {
+        const result = markdownToIR(input);
+        expect(result.text, `Input: ${JSON.stringify(input)}`).not.toMatch(/\n{3,}/);
+      }
+    });
+
+    it("multiple consecutive hrs between paragraphs should each render as separator", () => {
+      const input = `Para 1
+
+---
+
+---
+
+---
+
+Para 2`;
+      const result = markdownToIR(input);
+      expect(result.text).toBe("Para 1\n\n───\n\n───\n\n───\n\nPara 2");
+    });
+  });
+
+  describe("edge cases", () => {
+    it("hr between list items renders as separator without extra spacing", () => {
+      const input = `- Item 1
+- ---
+- Item 2`;
+      const result = markdownToIR(input);
+      expect(result.text).toBe("• Item 1\n\n───\n\n• Item 2");
+      expect(result.text).not.toMatch(/\n{3,}/);
+    });
+
+    it("hr followed immediately by heading", () => {
+      const input = `---
+
+# Heading
+
+Para`;
+      const result = markdownToIR(input);
+      // HR renders as separator, heading renders, para follows
+      expect(result.text).not.toMatch(/\n{3,}/);
+      expect(result.text).toContain("───");
+    });
+
+    it("heading followed by hr", () => {
+      const input = `# Heading
+
+---
+
+Para`;
+      const result = markdownToIR(input);
+      // Heading ends, HR renders, para follows
+      expect(result.text).not.toMatch(/\n{3,}/);
+      expect(result.text).toContain("───");
+    });
+  });
+});
diff --git a/src/markdown/ir.list-spacing.test.ts b/src/markdown/ir.list-spacing.test.ts
new file mode 100644
index 00000000000..56a8b3f174c
--- /dev/null
+++ b/src/markdown/ir.list-spacing.test.ts
@@ -0,0 +1,33 @@
+import { describe, it, expect } from "vitest";
+import { markdownToIR } from "./ir.js";
+
+describe("list paragraph spacing", () => {
+  it("adds blank line between bullet list and following paragraph", () => {
+    const input = `- item 1
+- item 2
+
+Paragraph after`;
+    const result = markdownToIR(input);
+    // Should have two newlines between "item 2" and "Paragraph"
+    expect(result.text).toContain("item 2\n\nParagraph");
+  });
+
+  it("adds blank line between ordered list and following paragraph", () => {
+    const input = `1. item 1
+2. item 2
+
+Paragraph after`;
+    const result = markdownToIR(input);
+    expect(result.text).toContain("item 2\n\nParagraph");
+  });
+
+  it("does not produce triple newlines", () => {
+    const input = `- item 1
+- item 2
+
+Paragraph after`;
+    const result = markdownToIR(input);
+    // Should NOT have three consecutive newlines
+    expect(result.text).not.toContain("\n\n\n");
+  });
+});
diff --git a/src/markdown/ir.nested-lists.test.ts b/src/markdown/ir.nested-lists.test.ts
new file mode 100644
index 00000000000..4ca4e9bd9d7
--- /dev/null
+++ b/src/markdown/ir.nested-lists.test.ts
@@ -0,0 +1,301 @@
+/**
+ * Nested List Rendering Tests
+ *
+ * This test file documents and validates the expected behavior for nested lists
+ * when rendering Markdown to plain text.
+ *
+ * ## Expected Plain Text Behavior
+ *
+ * Per CommonMark spec, nested lists create a hierarchical structure. When rendering
+ * to plain text for messaging platforms, we expect:
+ *
+ * 1. **Indentation**: Each nesting level adds 2 spaces of indentation
+ * 2. **Bullet markers**: Bullet lists use "•" (Unicode bullet)
+ * 3. **Ordered markers**: Ordered lists use "N. " format
+ * 4. **Line endings**: Each list item ends with a single newline
+ * 5. **List termination**: A trailing newline after the entire list (for top-level only)
+ *
+ * ## markdown-it Token Sequence
+ *
+ * For nested lists, markdown-it emits tokens in this order:
+ * - bullet_list_open (outer)
+ *   - list_item_open
+ *     - paragraph_open (hidden=true for tight lists)
+ *       - inline (with text children)
+ *     - paragraph_close
+ *     - bullet_list_open (nested)
+ *       - list_item_open
+ *         - paragraph_open
+ *           - inline
+ *         - paragraph_close
+ *       - list_item_close
+ *     - bullet_list_close
+ *   - list_item_close
+ * - bullet_list_close
+ *
+ * The key insight is that nested lists appear INSIDE the parent list_item,
+ * between the paragraph and the list_item_close.
+ */
+
+import { describe, it, expect } from "vitest";
+import { markdownToIR } from "./ir.js";
+
+describe("Nested Lists - 2 Level Nesting", () => {
+  it("renders bullet items nested inside bullet items with proper indentation", () => {
+    const input = `- Item 1
+  - Nested 1.1
+  - Nested 1.2
+- Item 2`;
+
+    const result = markdownToIR(input);
+
+    // Expected output:
+    // • Item 1
+    //   • Nested 1.1
+    //   • Nested 1.2
+    // • Item 2
+    // Note: markdownToIR trims trailing whitespace, so no final newline
+    const expected = `• Item 1
+  • Nested 1.1
+  • Nested 1.2
+• Item 2`;
+
+    expect(result.text).toBe(expected);
+  });
+
+  it("renders ordered items nested inside bullet items", () => {
+    const input = `- Bullet item
+  1. Ordered sub-item 1
+  2. Ordered sub-item 2
+- Another bullet`;
+
+    const result = markdownToIR(input);
+
+    // Expected output:
+    // • Bullet item
+    //   1. Ordered sub-item 1
+    //   2. Ordered sub-item 2
+    // • Another bullet
+    const expected = `• Bullet item
+  1. Ordered sub-item 1
+  2. Ordered sub-item 2
+• Another bullet`;
+
+    expect(result.text).toBe(expected);
+  });
+
+  it("renders bullet items nested inside ordered items", () => {
+    const input = `1. Ordered 1
+   - Bullet sub 1
+   - Bullet sub 2
+2. Ordered 2`;
+
+    const result = markdownToIR(input);
+
+    // Expected output:
+    // 1. Ordered 1
+    //   • Bullet sub 1
+    //   • Bullet sub 2
+    // 2. Ordered 2
+    const expected = `1. Ordered 1
+  • Bullet sub 1
+  • Bullet sub 2
+2. Ordered 2`;
+
+    expect(result.text).toBe(expected);
+  });
+
+  it("renders ordered items nested inside ordered items", () => {
+    const input = `1. First
+   1. Sub-first
+   2. Sub-second
+2. Second`;
+
+    const result = markdownToIR(input);
+
+    const expected = `1. First
+  1. Sub-first
+  2. Sub-second
+2. Second`;
+
+    expect(result.text).toBe(expected);
+  });
+});
+
+describe("Nested Lists - 3+ Level Deep Nesting", () => {
+  it("renders 3 levels of bullet nesting", () => {
+    const input = `- Level 1
+  - Level 2
+    - Level 3
+- Back to 1`;
+
+    const result = markdownToIR(input);
+
+    // Expected output with progressive indentation:
+    // • Level 1
+    //   • Level 2
+    //     • Level 3
+    // • Back to 1
+    const expected = `• Level 1
+  • Level 2
+    • Level 3
+• Back to 1`;
+
+    expect(result.text).toBe(expected);
+  });
+
+  it("renders 4 levels of bullet nesting", () => {
+    const input = `- L1
+  - L2
+    - L3
+      - L4
+- Back`;
+
+    const result = markdownToIR(input);
+
+    const expected = `• L1
+  • L2
+    • L3
+      • L4
+• Back`;
+
+    expect(result.text).toBe(expected);
+  });
+
+  it("renders 3 levels with multiple items at each level", () => {
+    const input = `- A1
+  - B1
+    - C1
+    - C2
+  - B2
+- A2`;
+
+    const result = markdownToIR(input);
+
+    const expected = `• A1
+  • B1
+    • C1
+    • C2
+  • B2
+• A2`;
+
+    expect(result.text).toBe(expected);
+  });
+});
+
+describe("Nested Lists - Mixed Nesting", () => {
+  it("renders complex mixed nesting (bullet > ordered > bullet)", () => {
+    const input = `- Bullet 1
+  1. Ordered 1.1
+     - Deep bullet
+  2. Ordered 1.2
+- Bullet 2`;
+
+    const result = markdownToIR(input);
+
+    const expected = `• Bullet 1
+  1. Ordered 1.1
+    • Deep bullet
+  2. Ordered 1.2
+• Bullet 2`;
+
+    expect(result.text).toBe(expected);
+  });
+
+  it("renders ordered > bullet > ordered nesting", () => {
+    const input = `1. First
+   - Sub bullet
+     1. Deep ordered
+   - Another bullet
+2. Second`;
+
+    const result = markdownToIR(input);
+
+    const expected = `1. First
+  • Sub bullet
+    1. Deep ordered
+  • Another bullet
+2. Second`;
+
+    expect(result.text).toBe(expected);
+  });
+});
+
+describe("Nested Lists - Newline Handling", () => {
+  it("does not produce triple newlines in nested lists", () => {
+    const input = `- Item 1
+  - Nested
+- Item 2`;
+
+    const result = markdownToIR(input);
+    expect(result.text).not.toContain("\n\n\n");
+  });
+
+  it("does not produce double newlines between nested items", () => {
+    const input = `- A
+  - B
+  - C
+- D`;
+
+    const result = markdownToIR(input);
+
+    // Between B and C there should be exactly one newline
+    expect(result.text).toContain("  • B\n  • C");
+    expect(result.text).not.toContain("  • B\n\n  • C");
+  });
+
+  it("properly terminates top-level list (trimmed output)", () => {
+    const input = `- Item 1
+  - Nested
+- Item 2`;
+
+    const result = markdownToIR(input);
+
+    // markdownToIR trims trailing whitespace, so output should end with Item 2
+    // (no trailing newline after trimming)
+    expect(result.text).toMatch(/Item 2$/);
+    // Should not have excessive newlines before Item 2
+    expect(result.text).not.toContain("\n\n• Item 2");
+  });
+});
+
+describe("Nested Lists - Edge Cases", () => {
+  it("handles empty parent with nested items", () => {
+    // This is a bit of an edge case - a list item that's just a marker followed by nested content
+    const input = `-
+  - Nested only
+- Normal`;
+
+    const result = markdownToIR(input);
+
+    // Should still render the nested item with proper indentation
+    expect(result.text).toContain("  • Nested only");
+  });
+
+  it("handles nested list as first child of parent item", () => {
+    const input = `- Parent text
+  - Child
+- Another parent`;
+
+    const result = markdownToIR(input);
+
+    // The child should appear indented under the parent
+    expect(result.text).toContain("• Parent text\n  • Child");
+  });
+
+  it("handles sibling nested lists at same level", () => {
+    const input = `- A
+  - A1
+- B
+  - B1`;
+
+    const result = markdownToIR(input);
+
+    const expected = `• A
+  • A1
+• B
+  • B1`;
+
+    expect(result.text).toBe(expected);
+  });
+});
diff --git a/src/markdown/ir.table-code.test.ts b/src/markdown/ir.table-code.test.ts
new file mode 100644
index 00000000000..5a52c3dd22c
--- /dev/null
+++ b/src/markdown/ir.table-code.test.ts
@@ -0,0 +1,89 @@
+import { describe, expect, it } from "vitest";
+import { markdownToIR } from "./ir.js";
+
+describe("markdownToIR tableMode code - style overlap", () => {
+  it("should not have overlapping styles when cell has bold text", () => {
+    const md = `
+| Name | Value |
+|------|-------|
+| **Bold** | Normal |
+`.trim();
+
+    const ir = markdownToIR(md, { tableMode: "code" });
+
+    // Check for overlapping styles
+    const codeBlockSpan = ir.styles.find((s) => s.style === "code_block");
+    const boldSpan = ir.styles.find((s) => s.style === "bold");
+
+    // Either:
+    // 1. There should be no bold spans in code mode (inner styles stripped), OR
+    // 2. If bold spans exist, they should not overlap with code_block span
+    if (codeBlockSpan && boldSpan) {
+      // Check for overlap
+      const overlaps = boldSpan.start < codeBlockSpan.end && boldSpan.end > codeBlockSpan.start;
+      // Overlapping styles are the bug - this should fail until fixed
+      expect(overlaps).toBe(false);
+    }
+  });
+
+  it("should not have overlapping styles when cell has italic text", () => {
+    const md = `
+| Name | Value |
+|------|-------|
+| *Italic* | Normal |
+`.trim();
+
+    const ir = markdownToIR(md, { tableMode: "code" });
+
+    const codeBlockSpan = ir.styles.find((s) => s.style === "code_block");
+    const italicSpan = ir.styles.find((s) => s.style === "italic");
+
+    if (codeBlockSpan && italicSpan) {
+      const overlaps = italicSpan.start < codeBlockSpan.end && italicSpan.end > codeBlockSpan.start;
+      expect(overlaps).toBe(false);
+    }
+  });
+
+  it("should not have overlapping styles when cell has inline code", () => {
+    const md = `
+| Name | Value |
+|------|-------|
+| \`code\` | Normal |
+`.trim();
+
+    const ir = markdownToIR(md, { tableMode: "code" });
+
+    const codeBlockSpan = ir.styles.find((s) => s.style === "code_block");
+    const codeSpan = ir.styles.find((s) => s.style === "code");
+
+    if (codeBlockSpan && codeSpan) {
+      const overlaps = codeSpan.start < codeBlockSpan.end && codeSpan.end > codeBlockSpan.start;
+      expect(overlaps).toBe(false);
+    }
+  });
+
+  it("should not have overlapping styles with multiple styled cells", () => {
+    const md = `
+| Name | Value |
+|------|-------|
+| **A** | *B* |
+| _C_ | ~~D~~ |
+`.trim();
+
+    const ir = markdownToIR(md, { tableMode: "code" });
+
+    const codeBlockSpan = ir.styles.find((s) => s.style === "code_block");
+    if (!codeBlockSpan) {
+      return;
+    }
+
+    // Check that no non-code_block style overlaps with code_block
+    for (const style of ir.styles) {
+      if (style.style === "code_block") {
+        continue;
+      }
+      const overlaps = style.start < codeBlockSpan.end && style.end > codeBlockSpan.start;
+      expect(overlaps).toBe(false);
+    }
+  });
+});
diff --git a/src/markdown/ir.ts b/src/markdown/ir.ts
index 37c15c198ad..f72d472b67f 100644
--- a/src/markdown/ir.ts
+++ b/src/markdown/ir.ts
@@ -364,6 +364,14 @@ function appendCell(state: RenderState, cell: TableCell) {
   }
 }
 
+function appendCellTextOnly(state: RenderState, cell: TableCell) {
+  if (!cell.text) {
+    return;
+  }
+  state.text += cell.text;
+  // Do not append styles - this is used for code blocks where inner styles would overlap
+}
+
 function renderTableAsBullets(state: RenderState) {
   if (!state.table) {
     return;
@@ -474,7 +482,8 @@ function renderTableAsCode(state: RenderState) {
       state.text += " ";
       const cell = cells[i];
       if (cell) {
-        appendCell(state, cell);
+        // Use text-only append to avoid overlapping styles with code_block
+        appendCellTextOnly(state, cell);
       }
       const pad = widths[i] - (cell?.text.length ?? 0);
       if (pad > 0) {
@@ -589,27 +598,43 @@ function renderTokens(tokens: MarkdownToken[], state: RenderState): void {
         break;
       case "blockquote_close":
         closeStyle(state, "blockquote");
-        state.text += "\n";
         break;
       case "bullet_list_open":
+        // Add newline before nested list starts (so nested items appear on new line)
+        if (state.env.listStack.length > 0) {
+          state.text += "\n";
+        }
         state.env.listStack.push({ type: "bullet", index: 0 });
         break;
       case "bullet_list_close":
         state.env.listStack.pop();
+        if (state.env.listStack.length === 0) {
+          state.text += "\n";
+        }
         break;
       case "ordered_list_open": {
+        // Add newline before nested list starts (so nested items appear on new line)
+        if (state.env.listStack.length > 0) {
+          state.text += "\n";
+        }
         const start = Number(getAttr(token, "start") ?? "1");
         state.env.listStack.push({ type: "ordered", index: start - 1 });
         break;
       }
       case "ordered_list_close":
         state.env.listStack.pop();
+        if (state.env.listStack.length === 0) {
+          state.text += "\n";
+        }
         break;
       case "list_item_open":
         appendListPrefix(state);
         break;
       case "list_item_close":
-        state.text += "\n";
+        // Avoid double newlines (nested list's last item already added newline)
+        if (!state.text.endsWith("\n")) {
+          state.text += "\n";
+        }
         break;
       case "code_block":
       case "fence":
@@ -680,7 +705,8 @@ function renderTokens(tokens: MarkdownToken[], state: RenderState): void {
         break;
 
       case "hr":
-        state.text += "\n";
+        // Render as a visual separator
+        state.text += "───\n\n";
         break;
       default:
         if (token.children) {
@@ -744,7 +770,13 @@ function mergeStyleSpans(spans: MarkdownStyleSpan[]): MarkdownStyleSpan[] {
   const merged: MarkdownStyleSpan[] = [];
   for (const span of sorted) {
     const prev = merged[merged.length - 1];
-    if (prev && prev.style === span.style && span.start <= prev.end) {
+    if (
+      prev &&
+      prev.style === span.style &&
+      // Blockquotes are container blocks. Adjacent blockquote spans should not merge or
+      // consecutive blockquotes can "style bleed" across the paragraph boundary.
+      (span.start < prev.end || (span.start === prev.end && span.style !== "blockquote"))
+    ) {
       prev.end = Math.max(prev.end, span.end);
       continue;
     }
diff --git a/src/signal/format.chunking.test.ts b/src/signal/format.chunking.test.ts
new file mode 100644
index 00000000000..ded30c842bb
--- /dev/null
+++ b/src/signal/format.chunking.test.ts
@@ -0,0 +1,390 @@
+import { describe, expect, it } from "vitest";
+import { markdownToSignalTextChunks } from "./format.js";
+
+describe("splitSignalFormattedText", () => {
+  // We test the internal chunking behavior via markdownToSignalTextChunks with
+  // pre-rendered SignalFormattedText. The helper is not exported, so we test
+  // it indirectly through integration tests and by constructing scenarios that
+  // exercise the splitting logic.
+
+  describe("style-aware splitting - basic text", () => {
+    it("text with no styles splits correctly at whitespace", () => {
+      // Create text that exceeds limit and must be split
+      const limit = 20;
+      const markdown = "hello world this is a test";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      expect(chunks.length).toBeGreaterThan(1);
+      for (const chunk of chunks) {
+        expect(chunk.text.length).toBeLessThanOrEqual(limit);
+      }
+      // Verify all text is preserved (joined chunks should contain all words)
+      const joinedText = chunks.map((c) => c.text).join(" ");
+      expect(joinedText).toContain("hello");
+      expect(joinedText).toContain("world");
+      expect(joinedText).toContain("test");
+    });
+
+    it("empty text returns empty array", () => {
+      // Empty input produces no chunks (not an empty chunk)
+      const chunks = markdownToSignalTextChunks("", 100);
+      expect(chunks).toEqual([]);
+    });
+
+    it("text under limit returns single chunk unchanged", () => {
+      const markdown = "short text";
+      const chunks = markdownToSignalTextChunks(markdown, 100);
+
+      expect(chunks).toHaveLength(1);
+      expect(chunks[0].text).toBe("short text");
+    });
+  });
+
+  describe("style-aware splitting - style preservation", () => {
+    it("style fully within first chunk stays in first chunk", () => {
+      // Create a message where bold text is in the first chunk
+      const limit = 30;
+      const markdown = "**bold** word more words here that exceed limit";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      expect(chunks.length).toBeGreaterThan(1);
+      // First chunk should contain the bold style
+      const firstChunk = chunks[0];
+      expect(firstChunk.text).toContain("bold");
+      expect(firstChunk.styles.some((s) => s.style === "BOLD")).toBe(true);
+      // The bold style should start at position 0 in the first chunk
+      const boldStyle = firstChunk.styles.find((s) => s.style === "BOLD");
+      expect(boldStyle).toBeDefined();
+      expect(boldStyle!.start).toBe(0);
+      expect(boldStyle!.length).toBe(4); // "bold"
+    });
+
+    it("style fully within second chunk has offset adjusted to chunk-local position", () => {
+      // Create a message where the styled text is in the second chunk
+      const limit = 30;
+      const markdown = "some filler text here **bold** at the end";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      expect(chunks.length).toBeGreaterThan(1);
+      // Find the chunk containing "bold"
+      const chunkWithBold = chunks.find((c) => c.text.includes("bold"));
+      expect(chunkWithBold).toBeDefined();
+      expect(chunkWithBold!.styles.some((s) => s.style === "BOLD")).toBe(true);
+
+      // The bold style should have chunk-local offset (not original text offset)
+      const boldStyle = chunkWithBold!.styles.find((s) => s.style === "BOLD");
+      expect(boldStyle).toBeDefined();
+      // The offset should be the position within this chunk, not the original text
+      const boldPos = chunkWithBold!.text.indexOf("bold");
+      expect(boldStyle!.start).toBe(boldPos);
+      expect(boldStyle!.length).toBe(4);
+    });
+
+    it("style spanning chunk boundary is split into two ranges", () => {
+      // Create text where a styled span crosses the chunk boundary
+      const limit = 15;
+      // "hello **bold text here** end" - the bold spans across chunk boundary
+      const markdown = "hello **boldtexthere** end";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      expect(chunks.length).toBeGreaterThan(1);
+
+      // Both chunks should have BOLD styles if the span was split
+      const chunksWithBold = chunks.filter((c) => c.styles.some((s) => s.style === "BOLD"));
+      // At least one chunk should have the bold style
+      expect(chunksWithBold.length).toBeGreaterThanOrEqual(1);
+
+      // For each chunk with bold, verify the style range is valid for that chunk
+      for (const chunk of chunksWithBold) {
+        for (const style of chunk.styles.filter((s) => s.style === "BOLD")) {
+          expect(style.start).toBeGreaterThanOrEqual(0);
+          expect(style.start + style.length).toBeLessThanOrEqual(chunk.text.length);
+        }
+      }
+    });
+
+    it("style starting exactly at split point goes entirely to second chunk", () => {
+      // Create text where style starts right at where we'd split
+      const limit = 10;
+      const markdown = "abcdefghi **bold**";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      expect(chunks.length).toBeGreaterThan(1);
+
+      // Find chunk with bold
+      const chunkWithBold = chunks.find((c) => c.styles.some((s) => s.style === "BOLD"));
+      expect(chunkWithBold).toBeDefined();
+
+      // Verify the bold style is valid within its chunk
+      const boldStyle = chunkWithBold!.styles.find((s) => s.style === "BOLD");
+      expect(boldStyle).toBeDefined();
+      expect(boldStyle!.start).toBeGreaterThanOrEqual(0);
+      expect(boldStyle!.start + boldStyle!.length).toBeLessThanOrEqual(chunkWithBold!.text.length);
+    });
+
+    it("style ending exactly at split point stays entirely in first chunk", () => {
+      const limit = 10;
+      const markdown = "**bold** rest of text";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // First chunk should have the complete bold style
+      const firstChunk = chunks[0];
+      if (firstChunk.text.includes("bold")) {
+        const boldStyle = firstChunk.styles.find((s) => s.style === "BOLD");
+        expect(boldStyle).toBeDefined();
+        expect(boldStyle!.start + boldStyle!.length).toBeLessThanOrEqual(firstChunk.text.length);
+      }
+    });
+
+    it("multiple styles, some spanning boundary, some not", () => {
+      const limit = 25;
+      // Mix of styles: italic at start, bold spanning boundary, monospace at end
+      const markdown = "_italic_ some text **bold text** and `code`";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      expect(chunks.length).toBeGreaterThan(1);
+
+      // Verify all style ranges are valid within their respective chunks
+      for (const chunk of chunks) {
+        for (const style of chunk.styles) {
+          expect(style.start).toBeGreaterThanOrEqual(0);
+          expect(style.start + style.length).toBeLessThanOrEqual(chunk.text.length);
+          expect(style.length).toBeGreaterThan(0);
+        }
+      }
+
+      // Collect all styles across chunks
+      const allStyles = chunks.flatMap((c) => c.styles.map((s) => s.style));
+      // We should have at least italic, bold, and monospace somewhere
+      expect(allStyles).toContain("ITALIC");
+      expect(allStyles).toContain("BOLD");
+      expect(allStyles).toContain("MONOSPACE");
+    });
+  });
+
+  describe("style-aware splitting - edge cases", () => {
+    it("handles zero-length text with styles gracefully", () => {
+      // Edge case: empty markdown produces no chunks
+      const chunks = markdownToSignalTextChunks("", 100);
+      expect(chunks).toHaveLength(0);
+    });
+
+    it("handles text that splits exactly at limit", () => {
+      const limit = 10;
+      const markdown = "1234567890"; // exactly 10 chars
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      expect(chunks).toHaveLength(1);
+      expect(chunks[0].text).toBe("1234567890");
+    });
+
+    it("preserves style through whitespace trimming", () => {
+      const limit = 30;
+      const markdown = "**bold**  some text that is longer than limit";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // Bold should be preserved in first chunk
+      const firstChunk = chunks[0];
+      if (firstChunk.text.includes("bold")) {
+        expect(firstChunk.styles.some((s) => s.style === "BOLD")).toBe(true);
+      }
+    });
+
+    it("handles repeated substrings correctly (no indexOf fragility)", () => {
+      // This test exposes the fragility of using indexOf to find chunk positions.
+      // If the same substring appears multiple times, indexOf finds the first
+      // occurrence, not necessarily the correct one.
+      const limit = 20;
+      // "word" appears multiple times - indexOf("word") would always find first
+      const markdown = "word **bold word** word more text here to chunk";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // Verify chunks are under limit
+      for (const chunk of chunks) {
+        expect(chunk.text.length).toBeLessThanOrEqual(limit);
+      }
+
+      // Find chunk(s) with bold style
+      const chunksWithBold = chunks.filter((c) => c.styles.some((s) => s.style === "BOLD"));
+      expect(chunksWithBold.length).toBeGreaterThanOrEqual(1);
+
+      // The bold style should correctly cover "bold word" (or part of it if split)
+      // and NOT incorrectly point to the first "word" in the text
+      for (const chunk of chunksWithBold) {
+        for (const style of chunk.styles.filter((s) => s.style === "BOLD")) {
+          const styledText = chunk.text.slice(style.start, style.start + style.length);
+          // The styled text should be part of "bold word", not the initial "word"
+          expect(styledText).toMatch(/^(bold( word)?|word)$/);
+          expect(style.start).toBeGreaterThanOrEqual(0);
+          expect(style.start + style.length).toBeLessThanOrEqual(chunk.text.length);
+        }
+      }
+    });
+
+    it("handles chunk that starts with whitespace after split", () => {
+      // When text is split at whitespace, the next chunk might have leading
+      // whitespace trimmed. Styles must account for this.
+      const limit = 15;
+      const markdown = "some text **bold** at end";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // All style ranges must be valid
+      for (const chunk of chunks) {
+        for (const style of chunk.styles) {
+          expect(style.start).toBeGreaterThanOrEqual(0);
+          expect(style.start + style.length).toBeLessThanOrEqual(chunk.text.length);
+        }
+      }
+    });
+
+    it("deterministically tracks position without indexOf fragility", () => {
+      // This test ensures the chunker doesn't rely on finding chunks via indexOf
+      // which can fail when chunkText trims whitespace or when duplicates exist.
+      // Create text with lots of whitespace and repeated patterns.
+      const limit = 25;
+      const markdown = "aaa   **bold**   aaa   **bold**   aaa extra text to force split";
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // Multiple chunks expected
+      expect(chunks.length).toBeGreaterThan(1);
+
+      // All chunks should respect limit
+      for (const chunk of chunks) {
+        expect(chunk.text.length).toBeLessThanOrEqual(limit);
+      }
+
+      // All style ranges must be valid within their chunks
+      for (const chunk of chunks) {
+        for (const style of chunk.styles) {
+          expect(style.start).toBeGreaterThanOrEqual(0);
+          expect(style.start + style.length).toBeLessThanOrEqual(chunk.text.length);
+          // The styled text at that position should actually be "bold"
+          if (style.style === "BOLD") {
+            const styledText = chunk.text.slice(style.start, style.start + style.length);
+            expect(styledText).toBe("bold");
+          }
+        }
+      }
+    });
+  });
+});
+
+describe("markdownToSignalTextChunks", () => {
+  describe("link expansion chunk limit", () => {
+    it("does not exceed chunk limit after link expansion", () => {
+      // Create text that is close to limit, with a link that will expand
+      const limit = 100;
+      // Create text that's 90 chars, leaving only 10 chars of headroom
+      const filler = "x".repeat(80);
+      // This link will expand from "[link](url)" to "link (https://example.com/very/long/path)"
+      const markdown = `${filler} [link](https://example.com/very/long/path/that/will/exceed/limit)`;
+
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      for (const chunk of chunks) {
+        expect(chunk.text.length).toBeLessThanOrEqual(limit);
+      }
+    });
+
+    it("handles multiple links near chunk boundary", () => {
+      const limit = 100;
+      const filler = "x".repeat(60);
+      const markdown = `${filler} [a](https://a.com) [b](https://b.com) [c](https://c.com)`;
+
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      for (const chunk of chunks) {
+        expect(chunk.text.length).toBeLessThanOrEqual(limit);
+      }
+    });
+  });
+
+  describe("link expansion with style preservation", () => {
+    it("long message with links that expand beyond limit preserves all text", () => {
+      const limit = 80;
+      const filler = "a".repeat(50);
+      const markdown = `${filler} [click here](https://example.com/very/long/path/to/page) more text`;
+
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // All chunks should be under limit
+      for (const chunk of chunks) {
+        expect(chunk.text.length).toBeLessThanOrEqual(limit);
+      }
+
+      // Combined text should contain all original content
+      const combined = chunks.map((c) => c.text).join("");
+      expect(combined).toContain(filler);
+      expect(combined).toContain("click here");
+      expect(combined).toContain("example.com");
+    });
+
+    it("styles (bold, italic) survive chunking correctly after link expansion", () => {
+      const limit = 60;
+      const markdown =
+        "**bold start** text [link](https://example.com/path) _italic_ more content here to force chunking";
+
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // Should have multiple chunks
+      expect(chunks.length).toBeGreaterThan(1);
+
+      // All style ranges should be valid within their chunks
+      for (const chunk of chunks) {
+        for (const style of chunk.styles) {
+          expect(style.start).toBeGreaterThanOrEqual(0);
+          expect(style.start + style.length).toBeLessThanOrEqual(chunk.text.length);
+          expect(style.length).toBeGreaterThan(0);
+        }
+      }
+
+      // Verify styles exist somewhere
+      const allStyles = chunks.flatMap((c) => c.styles.map((s) => s.style));
+      expect(allStyles).toContain("BOLD");
+      expect(allStyles).toContain("ITALIC");
+    });
+
+    it("multiple links near chunk boundary all get properly chunked", () => {
+      const limit = 50;
+      const markdown =
+        "[first](https://first.com/long/path) [second](https://second.com/another/path) [third](https://third.com)";
+
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // All chunks should respect limit
+      for (const chunk of chunks) {
+        expect(chunk.text.length).toBeLessThanOrEqual(limit);
+      }
+
+      // All link labels should appear somewhere
+      const combined = chunks.map((c) => c.text).join("");
+      expect(combined).toContain("first");
+      expect(combined).toContain("second");
+      expect(combined).toContain("third");
+    });
+
+    it("preserves spoiler style through link expansion and chunking", () => {
+      const limit = 40;
+      const markdown =
+        "||secret content|| and [link](https://example.com/path) with more text to chunk";
+
+      const chunks = markdownToSignalTextChunks(markdown, limit);
+
+      // All chunks should respect limit
+      for (const chunk of chunks) {
+        expect(chunk.text.length).toBeLessThanOrEqual(limit);
+      }
+
+      // Spoiler style should exist and be valid
+      const chunkWithSpoiler = chunks.find((c) => c.styles.some((s) => s.style === "SPOILER"));
+      expect(chunkWithSpoiler).toBeDefined();
+
+      const spoilerStyle = chunkWithSpoiler!.styles.find((s) => s.style === "SPOILER");
+      expect(spoilerStyle).toBeDefined();
+      expect(spoilerStyle!.start).toBeGreaterThanOrEqual(0);
+      expect(spoilerStyle!.start + spoilerStyle!.length).toBeLessThanOrEqual(
+        chunkWithSpoiler!.text.length,
+      );
+    });
+  });
+});
diff --git a/src/signal/format.links.test.ts b/src/signal/format.links.test.ts
new file mode 100644
index 00000000000..7ef77e71db5
--- /dev/null
+++ b/src/signal/format.links.test.ts
@@ -0,0 +1,58 @@
+import { describe, expect, it } from "vitest";
+import { markdownToSignalText } from "./format.js";
+
+describe("markdownToSignalText", () => {
+  describe("duplicate URL display", () => {
+    it("does not duplicate URL when label matches URL without protocol", () => {
+      // [selfh.st](http://selfh.st) should render as "selfh.st" not "selfh.st (http://selfh.st)"
+      const res = markdownToSignalText("[selfh.st](http://selfh.st)");
+      expect(res.text).toBe("selfh.st");
+    });
+
+    it("does not duplicate URL when label matches URL without https protocol", () => {
+      const res = markdownToSignalText("[example.com](https://example.com)");
+      expect(res.text).toBe("example.com");
+    });
+
+    it("does not duplicate URL when label matches URL without www prefix", () => {
+      const res = markdownToSignalText("[www.example.com](https://example.com)");
+      expect(res.text).toBe("www.example.com");
+    });
+
+    it("does not duplicate URL when label matches URL without trailing slash", () => {
+      const res = markdownToSignalText("[example.com](https://example.com/)");
+      expect(res.text).toBe("example.com");
+    });
+
+    it("does not duplicate URL when label matches URL with multiple trailing slashes", () => {
+      const res = markdownToSignalText("[example.com](https://example.com///)");
+      expect(res.text).toBe("example.com");
+    });
+
+    it("does not duplicate URL when label includes www but URL does not", () => {
+      const res = markdownToSignalText("[example.com](https://www.example.com)");
+      expect(res.text).toBe("example.com");
+    });
+
+    it("handles case-insensitive domain comparison", () => {
+      const res = markdownToSignalText("[EXAMPLE.COM](https://example.com)");
+      expect(res.text).toBe("EXAMPLE.COM");
+    });
+
+    it("still shows URL when label is meaningfully different", () => {
+      const res = markdownToSignalText("[click here](https://example.com)");
+      expect(res.text).toBe("click here (https://example.com)");
+    });
+
+    it("handles URL with path - should show URL when label is just domain", () => {
+      // Label is just domain, URL has path - these are meaningfully different
+      const res = markdownToSignalText("[example.com](https://example.com/page)");
+      expect(res.text).toBe("example.com (https://example.com/page)");
+    });
+
+    it("does not duplicate when label matches full URL with path", () => {
+      const res = markdownToSignalText("[example.com/page](https://example.com/page)");
+      expect(res.text).toBe("example.com/page");
+    });
+  });
+});
diff --git a/src/signal/format.test.ts b/src/signal/format.test.ts
index 40e509fa891..e22a6607f99 100644
--- a/src/signal/format.test.ts
+++ b/src/signal/format.test.ts
@@ -21,6 +21,18 @@ describe("markdownToSignalText", () => {
     expect(res.styles).toEqual([]);
   });
 
+  it("keeps style offsets correct with multiple expanded links", () => {
+    const markdown =
+      "[first](https://example.com/first) **bold** [second](https://example.com/second)";
+    const res = markdownToSignalText(markdown);
+
+    const expectedText =
+      "first (https://example.com/first) bold second (https://example.com/second)";
+
+    expect(res.text).toBe(expectedText);
+    expect(res.styles).toEqual([{ start: expectedText.indexOf("bold"), length: 4, style: "BOLD" }]);
+  });
+
   it("applies spoiler styling", () => {
     const res = markdownToSignalText("hello ||secret|| world");
 
diff --git a/src/signal/format.ts b/src/signal/format.ts
index f310b75a6ee..8f35a34f2da 100644
--- a/src/signal/format.ts
+++ b/src/signal/format.ts
@@ -34,6 +34,17 @@ type Insertion = {
   length: number;
 };
 
+function normalizeUrlForComparison(url: string): string {
+  let normalized = url.toLowerCase();
+  // Strip protocol
+  normalized = normalized.replace(/^https?:\/\//, "");
+  // Strip www. prefix
+  normalized = normalized.replace(/^www\./, "");
+  // Strip trailing slashes
+  normalized = normalized.replace(/\/+$/, "");
+  return normalized;
+}
+
 function mapStyle(style: MarkdownStyle): SignalTextStyle | null {
   switch (style) {
     case "bold":
@@ -100,15 +111,17 @@ function applyInsertionsToStyles(
   }
   const sortedInsertions = [...insertions].toSorted((a, b) => a.pos - b.pos);
   let updated = spans;
+  let cumulativeShift = 0;
 
   for (const insertion of sortedInsertions) {
+    const insertionPos = insertion.pos + cumulativeShift;
     const next: SignalStyleSpan[] = [];
     for (const span of updated) {
-      if (span.end <= insertion.pos) {
+      if (span.end <= insertionPos) {
         next.push(span);
         continue;
       }
-      if (span.start >= insertion.pos) {
+      if (span.start >= insertionPos) {
         next.push({
           start: span.start + insertion.length,
           end: span.end + insertion.length,
@@ -116,15 +129,15 @@ function applyInsertionsToStyles(
         });
         continue;
       }
-      if (span.start < insertion.pos && span.end > insertion.pos) {
-        if (insertion.pos > span.start) {
+      if (span.start < insertionPos && span.end > insertionPos) {
+        if (insertionPos > span.start) {
           next.push({
             start: span.start,
-            end: insertion.pos,
+            end: insertionPos,
             style: span.style,
           });
         }
-        const shiftedStart = insertion.pos + insertion.length;
+        const shiftedStart = insertionPos + insertion.length;
         const shiftedEnd = span.end + insertion.length;
         if (shiftedEnd > shiftedStart) {
           next.push({
@@ -136,6 +149,7 @@ function applyInsertionsToStyles(
       }
     }
     updated = next;
+    cumulativeShift += insertion.length;
   }
 
   return updated;
@@ -161,16 +175,26 @@ function renderSignalText(ir: MarkdownIR): SignalFormattedText {
     const href = link.href.trim();
     const label = text.slice(link.start, link.end);
     const trimmedLabel = label.trim();
-    const comparableHref = href.startsWith("mailto:") ? href.slice("mailto:".length) : href;
 
     if (href) {
       if (!trimmedLabel) {
         out += href;
         insertions.push({ pos: link.end, length: href.length });
-      } else if (trimmedLabel !== href && trimmedLabel !== comparableHref) {
-        const addition = ` (${href})`;
-        out += addition;
-        insertions.push({ pos: link.end, length: addition.length });
+      } else {
+        // Check if label is similar enough to URL that showing both would be redundant
+        const normalizedLabel = normalizeUrlForComparison(trimmedLabel);
+        let comparableHref = href;
+        if (href.startsWith("mailto:")) {
+          comparableHref = href.slice("mailto:".length);
+        }
+        const normalizedHref = normalizeUrlForComparison(comparableHref);
+
+        // Only show URL if label is meaningfully different from it
+        if (normalizedLabel !== normalizedHref) {
+          const addition = ` (${href})`;
+          out += addition;
+          insertions.push({ pos: link.end, length: addition.length });
+        }
       }
     }
 
@@ -214,13 +238,136 @@ export function markdownToSignalText(
   const ir = markdownToIR(markdown ?? "", {
     linkify: true,
     enableSpoilers: true,
-    headingStyle: "none",
-    blockquotePrefix: "",
+    headingStyle: "bold",
+    blockquotePrefix: "> ",
     tableMode: options.tableMode,
   });
   return renderSignalText(ir);
 }
 
+function sliceSignalStyles(
+  styles: SignalTextStyleRange[],
+  start: number,
+  end: number,
+): SignalTextStyleRange[] {
+  const sliced: SignalTextStyleRange[] = [];
+  for (const style of styles) {
+    const styleEnd = style.start + style.length;
+    const sliceStart = Math.max(style.start, start);
+    const sliceEnd = Math.min(styleEnd, end);
+    if (sliceEnd > sliceStart) {
+      sliced.push({
+        start: sliceStart - start,
+        length: sliceEnd - sliceStart,
+        style: style.style,
+      });
+    }
+  }
+  return sliced;
+}
+
+/**
+ * Split Signal formatted text into chunks under the limit while preserving styles.
+ *
+ * This implementation deterministically tracks cursor position without using indexOf,
+ * which is fragile when chunks are trimmed or when duplicate substrings exist.
+ * Styles spanning chunk boundaries are split into separate ranges for each chunk.
+ */
+function splitSignalFormattedText(
+  formatted: SignalFormattedText,
+  limit: number,
+): SignalFormattedText[] {
+  const { text, styles } = formatted;
+
+  if (text.length <= limit) {
+    return [formatted];
+  }
+
+  const results: SignalFormattedText[] = [];
+  let remaining = text;
+  let offset = 0; // Track position in original text for style slicing
+
+  while (remaining.length > 0) {
+    if (remaining.length <= limit) {
+      // Last chunk - take everything remaining
+      const trimmed = remaining.trimEnd();
+      if (trimmed.length > 0) {
+        results.push({
+          text: trimmed,
+          styles: mergeStyles(sliceSignalStyles(styles, offset, offset + trimmed.length)),
+        });
+      }
+      break;
+    }
+
+    // Find a good break point within the limit
+    const window = remaining.slice(0, limit);
+    let breakIdx = findBreakIndex(window);
+
+    // If no good break point found, hard break at limit
+    if (breakIdx <= 0) {
+      breakIdx = limit;
+    }
+
+    // Extract chunk and trim trailing whitespace
+    const rawChunk = remaining.slice(0, breakIdx);
+    const chunk = rawChunk.trimEnd();
+
+    if (chunk.length > 0) {
+      results.push({
+        text: chunk,
+        styles: mergeStyles(sliceSignalStyles(styles, offset, offset + chunk.length)),
+      });
+    }
+
+    // Advance past the chunk and any whitespace separator
+    const brokeOnWhitespace = breakIdx < remaining.length && /\s/.test(remaining[breakIdx]);
+    const nextStart = Math.min(remaining.length, breakIdx + (brokeOnWhitespace ? 1 : 0));
+
+    // Chunks are sent as separate messages, so we intentionally drop boundary whitespace.
+    // Keep `offset` in sync with the dropped characters so style slicing stays correct.
+    remaining = remaining.slice(nextStart).trimStart();
+    offset = text.length - remaining.length;
+  }
+
+  return results;
+}
+
+/**
+ * Find the best break index within a text window.
+ * Prefers newlines over whitespace, avoids breaking inside parentheses.
+ */
+function findBreakIndex(window: string): number {
+  let lastNewline = -1;
+  let lastWhitespace = -1;
+  let parenDepth = 0;
+
+  for (let i = 0; i < window.length; i++) {
+    const char = window[i];
+
+    if (char === "(") {
+      parenDepth++;
+      continue;
+    }
+    if (char === ")" && parenDepth > 0) {
+      parenDepth--;
+      continue;
+    }
+
+    // Only consider break points outside parentheses
+    if (parenDepth === 0) {
+      if (char === "\n") {
+        lastNewline = i;
+      } else if (/\s/.test(char)) {
+        lastWhitespace = i;
+      }
+    }
+  }
+
+  // Prefer newline break, fall back to whitespace
+  return lastNewline > 0 ? lastNewline : lastWhitespace;
+}
+
 export function markdownToSignalTextChunks(
   markdown: string,
   limit: number,
@@ -229,10 +376,22 @@ export function markdownToSignalTextChunks(
   const ir = markdownToIR(markdown ?? "", {
     linkify: true,
     enableSpoilers: true,
-    headingStyle: "none",
-    blockquotePrefix: "",
+    headingStyle: "bold",
+    blockquotePrefix: "> ",
     tableMode: options.tableMode,
   });
   const chunks = chunkMarkdownIR(ir, limit);
-  return chunks.map((chunk) => renderSignalText(chunk));
+  const results: SignalFormattedText[] = [];
+
+  for (const chunk of chunks) {
+    const rendered = renderSignalText(chunk);
+    // If link expansion caused the chunk to exceed the limit, re-chunk it
+    if (rendered.text.length > limit) {
+      results.push(...splitSignalFormattedText(rendered, limit));
+    } else {
+      results.push(rendered);
+    }
+  }
+
+  return results;
 }
diff --git a/src/signal/format.visual.test.ts b/src/signal/format.visual.test.ts
new file mode 100644
index 00000000000..78f913b7945
--- /dev/null
+++ b/src/signal/format.visual.test.ts
@@ -0,0 +1,57 @@
+import { describe, expect, it } from "vitest";
+import { markdownToSignalText } from "./format.js";
+
+describe("markdownToSignalText", () => {
+  describe("headings visual distinction", () => {
+    it("renders headings as bold text", () => {
+      const res = markdownToSignalText("# Heading 1");
+      expect(res.text).toBe("Heading 1");
+      expect(res.styles).toContainEqual({ start: 0, length: 9, style: "BOLD" });
+    });
+
+    it("renders h2 headings as bold text", () => {
+      const res = markdownToSignalText("## Heading 2");
+      expect(res.text).toBe("Heading 2");
+      expect(res.styles).toContainEqual({ start: 0, length: 9, style: "BOLD" });
+    });
+
+    it("renders h3 headings as bold text", () => {
+      const res = markdownToSignalText("### Heading 3");
+      expect(res.text).toBe("Heading 3");
+      expect(res.styles).toContainEqual({ start: 0, length: 9, style: "BOLD" });
+    });
+  });
+
+  describe("blockquote visual distinction", () => {
+    it("renders blockquotes with a visible prefix", () => {
+      const res = markdownToSignalText("> This is a quote");
+      // Should have some kind of prefix to distinguish it
+      expect(res.text).toMatch(/^[│>]/);
+      expect(res.text).toContain("This is a quote");
+    });
+
+    it("renders multi-line blockquotes with prefix", () => {
+      const res = markdownToSignalText("> Line 1\n> Line 2");
+      // Should start with the prefix
+      expect(res.text).toMatch(/^[│>]/);
+      expect(res.text).toContain("Line 1");
+      expect(res.text).toContain("Line 2");
+    });
+  });
+
+  describe("horizontal rule rendering", () => {
+    it("renders horizontal rules as a visible separator", () => {
+      const res = markdownToSignalText("Para 1\n\n---\n\nPara 2");
+      // Should contain some kind of visual separator like ───
+      expect(res.text).toMatch(/[─—-]{3,}/);
+    });
+
+    it("renders horizontal rule between content", () => {
+      const res = markdownToSignalText("Above\n\n***\n\nBelow");
+      expect(res.text).toContain("Above");
+      expect(res.text).toContain("Below");
+      // Should have a separator
+      expect(res.text).toMatch(/[─—-]{3,}/);
+    });
+  });
+});
diff --git a/src/slack/format.test.ts b/src/slack/format.test.ts
index 7ccda8e8758..eebb2bbf79b 100644
--- a/src/slack/format.test.ts
+++ b/src/slack/format.test.ts
@@ -82,10 +82,10 @@ describe("markdownToSlackMrkdwn", () => {
     expect(res).toBe("> Quote");
   });
 
-  it("handles adjacent list items", () => {
+  it("handles nested list items", () => {
     const res = markdownToSlackMrkdwn("- item\n  - nested");
-    // markdown-it treats indented items as continuation, not nesting
-    expect(res).toBe("• item  • nested");
+    // markdown-it correctly parses this as a nested list
+    expect(res).toBe("• item\n  • nested");
   });
 
   it("handles complex message with multiple elements", () => {