diff --git a/app/Tests/Markdown/Parse.hs b/app/Tests/Markdown/Parse.hs
index 56e8597..3b97f74 100644
--- a/app/Tests/Markdown/Parse.hs
+++ b/app/Tests/Markdown/Parse.hs
@@ -22,7 +22,15 @@ import Text.Megaparsec
 main :: IO ()
 main = do
   cond <-
-    checkParallel $ Group "Parse Tests" [("all_compile", all_compiles)]
+    checkParallel $
+      Group
+        "Parse Tests"
+        [ ("all_compile", all_compiles),
+          ("header_and_paragraph", header_and_paragraph),
+          ("paragraph_and_header_and_paragraph", paragraph_and_header_and_paragraph),
+          ("bold_and_header_and_paragraph", bold_and_header_and_paragraph),
+          ("code_block", code_block)
+        ]
   if cond
     then exitSuccess
     else exitFailure
@@ -35,3 +43,79 @@ all_compiles = property $ do
   case parsed of
     Right _ -> success
     Left e -> fail $ errorBundlePretty e
+
+header_and_paragraph :: Property
+header_and_paragraph = property $ do
+  header_text <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+  header_level <- forAll $ Gen.int (Range.linear 1 6)
+  paragraph_text <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+
+  let input = (T.pack $ take header_level $ repeat '#') <> header_text <> "\n\n" <> paragraph_text
+
+  let parsed = parse (Markdown.document :: ParsecT Void Text Identity IR.Document) "test_input" input
+
+  case parsed of
+    Right (Doc [Heading (H {level = header_level, text = [Text (header_text)]}), Paragraph (P ([Text paragraph_text]))]) -> success
+    Right tree -> fail $ "Incorrect syntax tree: " <> show tree
+    Left e -> fail $ errorBundlePretty e
+
+paragraph_and_header_and_paragraph :: Property
+paragraph_and_header_and_paragraph = property $ do
+  paragraph1_text <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+  header_text <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+  header_level <- forAll $ Gen.int (Range.linear 1 6)
+  paragraph2_text <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+
+  let input = paragraph1_text <> "\n\n" <> (T.pack $ take header_level $ repeat '#') <> header_text <> "\n\n" <> paragraph2_text
+
+  let parsed = parse (Markdown.document :: ParsecT Void Text Identity IR.Document) "test_input" input
+
+  case parsed of
+    Right (Doc [Paragraph (P ([Text paragarph1_text])), Heading (H {level = header_level, text = [Text (header_text)]}), Paragraph (P ([Text paragraph2_text]))]) -> success
+    Right tree -> fail $ "Incorrect syntax tree: " <> show tree
+    Left e -> fail $ errorBundlePretty e
+
+bold_and_header_and_paragraph :: Property
+bold_and_header_and_paragraph = property $ do
+  bold_text <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+  header_text <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+  header_level <- forAll $ Gen.int (Range.linear 1 6)
+  paragraph_text <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+
+  let input = "**" <> bold_text <> "**\n\n" <> (T.pack $ take header_level $ repeat '#') <> header_text <> "\n\n" <> paragraph_text
+
+  let parsed = parse (Markdown.document :: ParsecT Void Text Identity IR.Document) "test_input" input
+
+  case parsed of
+    Right (Doc [Paragraph (P ([Bold [Text bold_text]])), Heading (H {level = header_level, text = [Text (header_text)]}), Paragraph (P ([Text paragraph_text]))]) -> success
+    Right tree -> fail $ "Incorrect syntax tree: " <> show tree
+    Left e -> fail $ errorBundlePretty e
+
+code_block :: Property
+code_block = property $ do
+  language <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+  code <- forAll $ Gen.text (Range.linear 1 10) Gen.alpha
+  let input = "```" <> language <> "\n" <> code <> "```"
+
+  let parsed = parse (Markdown.document :: ParsecT Void Text Identity IR.Document) "test_input" input
+
+  case parsed of
+    Right (Doc [Code (C {language, code})]) -> success
+    Right tree -> fail $ "Incorrect syntax tree: " <> show tree
+    Left e -> fail $ errorBundlePretty e
+
+-- from new writing learning
+-- Error case, joins block quotes toegether
+-- > [*Sic*](https://www.merriam-webster.com/dictionary/sic) usually appears in parentheses or brackets, sometimes with the letters in italics. In this context it means “intentionally so written.” On its own, *sic* means “so” or “thus” and can be found in phrases such as *sic transit gloria mundi* ("so passes away the glory of the world") and *sic semper tyrannis* ("thus ever to tyrants," the motto of the state of Virginia).
+--
+-- > What is denoted by *sic* is that the word or phrase that precedes it occurs in the original passage being quoted or name being used and was not introduced by the writer doing the quoting.
+--
+
+-- from micro blogs
+-- Error case 2: made one bullet instead of two, happens for any number of items and probably applicable to numbered list as well
+-- - item 1
+-- - item 2
+
+-- From weekly notes, doing a header after a unordered list causes it to be seens as an inline element
+--
+-- From all-projects, not sure if it's block or what causing HTML escapes to go haywire