diff --git a/src/mdformat/renderer/_context.py b/src/mdformat/renderer/_context.py
index 238dd07d..c38315f5 100644
--- a/src/mdformat/renderer/_context.py
+++ b/src/mdformat/renderer/_context.py
@@ -459,6 +459,11 @@ def paragraph(node: RenderTreeNode, context: RenderContext) -> str:  # noqa: C90
         elif all(c == "=" for c in stripped):
             lines[i] = lines[i].replace("=", "\\=", 1)
 
+        # Make sure a paragraph line does not start with three or more
+        # tildes (otherwise it will be interpreted as a fenced code block).
+        if re.match(r"~{3,}", lines[i]):
+            lines[i] = f"\\{lines[i]}"
+
         # Check if the line could be interpreted as an HTML block.
         # If yes, prefix it with 4 spaces to prevent this.
         for html_seq_tuple in HTML_SEQUENCES:
diff --git a/tests/data/wrap_width_50.md b/tests/data/wrap_width_50.md
index eceede9f..be9fa55c 100644
--- a/tests/data/wrap_width_50.md
+++ b/tests/data/wrap_width_50.md
@@ -188,3 +188,33 @@ Starts with encoded space
 .
  * * \*
 .
+
+
+Wrap three tildes to line start (issue #590)
+.
+AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA ~~~ BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB
+.
+AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA
+\~~~
+BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB
+.
+
+
+Wrap two tildes to line start
+.
+AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA ~~ BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB
+.
+AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA
+~~
+BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB
+.
+
+
+Wrap four tildes to line start
+.
+AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA ~~~~ BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB
+.
+AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA
+\~~~~
+BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB
+.