From 2e40be16e47141a79e5e26eed92329f5ef3a7bea Mon Sep 17 00:00:00 2001
From: Josh Rose <1677846+JoshTheWanderer@users.noreply.github.com>
Date: Fri, 23 Jan 2026 15:34:16 +0100
Subject: [PATCH 1/2] fix: allow italic and bold at the start of a message

---
 app/helpers/content_filters/markdown_filter.rb | 2 +-
 test/helpers/content_filters_test.rb           | 5 +++++
 2 files changed, 6 insertions(+), 1 deletion(-)

diff --git a/app/helpers/content_filters/markdown_filter.rb b/app/helpers/content_filters/markdown_filter.rb
index 5aad59fc..09709e7a 100644
--- a/app/helpers/content_filters/markdown_filter.rb
+++ b/app/helpers/content_filters/markdown_filter.rb
@@ -12,7 +12,7 @@ class ContentFilters::MarkdownFilter < ActionText::Content::Filter
   # 2. Use backslash escaping: \*\*not bold\*\* → renders as **not bold** (plain text)
   MARKDOWN_PATTERNS = [
     /\*\*[^*]+\*\*/,                    # Bold: **text**
-    /(?<!^)\*[^*\s][^*]*\*/m,           # Italic: *text* (not at line start to avoid "* list items")
+    /(?<!\*)\*(?![*\s])[^*]+\*(?!\*)/,   # Italic: *text* (lookarounds avoid **bold** and "* list items")
     /`[^`]+`/,                          # Inline code: `code`
     /```[\s\S]+?```/,                   # Code blocks: ```code```
     /^[#]{1,6}\s/m,                     # Header levels 1-6: # Header
diff --git a/test/helpers/content_filters_test.rb b/test/helpers/content_filters_test.rb
index 82bfe2ad..8b0456bd 100644
--- a/test/helpers/content_filters_test.rb
+++ b/test/helpers/content_filters_test.rb
@@ -103,6 +103,11 @@ class ContentFiltersTest < ActionView::TestCase
     assert_markdown_rendered "This is *italic* text", /<em>italic<\/em>/
   end
 
+  test "renders italic text at line start" do
+    assert_markdown_applicable "*italic* at start"
+    assert_markdown_rendered "*italic* at start", /<em>italic<\/em>/
+  end
+
   test "renders inline code with backticks" do
     assert_markdown_rendered "Use the `print()` function", /<code>print\(\)<\/code>/
   end

From 57d29467d2815fcd2325d8bcb8d6af4f4306167f Mon Sep 17 00:00:00 2001
From: Josh Rose <1677846+JoshTheWanderer@users.noreply.github.com>
Date: Fri, 23 Jan 2026 15:37:23 +0100
Subject: [PATCH 2/2] test: add test for multi-line italic rendering

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>
---
 test/helpers/content_filters_test.rb | 8 ++++++++
 1 file changed, 8 insertions(+)

diff --git a/test/helpers/content_filters_test.rb b/test/helpers/content_filters_test.rb
index 8b0456bd..b9b5da6e 100644
--- a/test/helpers/content_filters_test.rb
+++ b/test/helpers/content_filters_test.rb
@@ -108,6 +108,14 @@ class ContentFiltersTest < ActionView::TestCase
     assert_markdown_rendered "*italic* at start", /<em>italic<\/em>/
   end
 
+  test "renders italic text spanning multiple lines" do
+    multiline_italic = "*italic text\nacross lines*"
+    assert_markdown_applicable multiline_italic
+    filtered = apply_text_filters(multiline_italic)
+    assert_match /<em>italic text/, filtered.to_html
+    assert_match /across lines<\/em>/, filtered.to_html
+  end
+
   test "renders inline code with backticks" do
     assert_markdown_rendered "Use the `print()` function", /<code>print\(\)<\/code>/
   end