diff --git a/src/parse.test.ts b/src/parse.test.ts
index 4e3c500..ad5ecc4 100644
--- a/src/parse.test.ts
+++ b/src/parse.test.ts
@@ -112,6 +112,21 @@ describe("parse", () => {
     expect(result.commands[0]!.expected).toEqual(["$ hello"])
   })
 
+  test("multiple escaped dollar signs", () => {
+    const content = "$ printf '$ a\\n$ b\\n'\n\\$ a\n\\$ b\n"
+    const result = parse("test.shout", content)
+    expect(result.commands).toHaveLength(1)
+    expect(result.commands[0]!.expected).toEqual(["$ a", "$ b"])
+  })
+
+  test("escaped dollar before first command is ignored", () => {
+    const content = "\\$ not a command\n$ echo hi\nhi\n"
+    const result = parse("test.shout", content)
+    // \$ before any command — no current command to attach to, so skipped
+    expect(result.commands).toHaveLength(1)
+    expect(result.commands[0]!.expected).toEqual(["hi"])
+  })
+
   test("no directives returns empty array", () => {
     const result = parse("test.shout", "$ echo hi\nhi\n")
     expect(result.directives).toEqual([])
diff --git a/test/dollar-sign-output.shout b/test/dollar-sign-output.shout
new file mode 100644
index 0000000..e41109c
--- /dev/null
+++ b/test/dollar-sign-output.shout
@@ -0,0 +1,9 @@
+$ echo '$ hello world'
+\$ hello world
+
+$ printf '$ line one\n$ line two\n'
+\$ line one
+\$ line two
+
+$ echo 'no dollar here'
+no dollar here