diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3961246..49e0513 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -50,6 +50,10 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   and nested arrays of tables: `[[a]]`, `b.c = 1`, `[[a]]`, `[a.b]` parses, as
   the TOML examples in the spec shape it. The records of the previous element
   falsely rejected the same paths in the next one.
+- `UseLiteralMultiline` falls back to the escaped basic string when the value
+  cannot be carried verbatim by the literal form: a run of three single quotes,
+  a control character, or a lone carriage return. Such values previously
+  produced output that did not re-parse.
 - A float with an exponent marker but no digits (`1e`, `0.0E`) is rejected;
   the exponent requires at least one digit.
 - A date-time offset outside 00:00 through 23:59 is rejected; such offsets
diff --git a/docs/API.md b/docs/API.md
index 7718ed5..e2ff056 100644
--- a/docs/API.md
+++ b/docs/API.md
@@ -351,7 +351,10 @@ out, err := interpres.NewEncoder().UseLiteralMultiline(80).Marshal(cfg)
 ```
 
 Single-line strings keep the basic form regardless of the threshold, and a
-threshold of `0` or less disables the option.
+threshold of `0` or less disables the option. A string the literal form cannot
+carry verbatim (an embedded run of three single quotes, a control character
+other than tab, or a carriage return outside a CRLF pair) also keeps the basic
+form, so the output always re-parses to the same value.
 
 ### Cancellation
 
diff --git a/encode.go b/encode.go
index bf876dd..8537add 100644
--- a/encode.go
+++ b/encode.go
@@ -798,12 +798,40 @@ func (e *encoder) writeInlineTable(m map[string]any) error {
 }
 
 func (e *encoder) writeStringVal(s string) error {
-	if e.opts.literalMultilineAt > 0 && strings.ContainsRune(s, '\n') && len(s) >= e.opts.literalMultilineAt {
+	if e.opts.literalMultilineAt > 0 && strings.ContainsRune(s, '\n') &&
+		len(s) >= e.opts.literalMultilineAt && canBeLiteralMultiline(s) {
 		return writeLiteralMultilineString(&e.buf, s)
 	}
 	return writeQuotedString(&e.buf, s)
 }
 
+// canBeLiteralMultiline reports whether s can be carried verbatim by the
+// literal ”'...”' form: the form has no escapes, so a run of three single
+// quotes would close the delimiter early, and control characters beyond tab,
+// and a carriage return outside a CRLF pair, have no representation at all.
+// Anything else falls back to the escaped basic string.
+func canBeLiteralMultiline(s string) bool {
+	if strings.Contains(s, "'''") {
+		return false
+	}
+	for i := 0; i < len(s); {
+		r, size := utf8.DecodeRuneInString(s[i:])
+		switch {
+		case r == '\t' || r == '\n':
+		case r == '\r':
+			if !strings.HasPrefix(s[i+size:], "\n") {
+				return false
+			}
+		default:
+			if r < 0x20 || r == 0x7f {
+				return false
+			}
+		}
+		i += size
+	}
+	return true
+}
+
 // writeLiteralMultilineString writes s as a TOML literal multi-line string,
 // surrounded by triple single quotes. The opening delimiter is followed by a
 // newline that the reader trims, so we always include one. The closing
diff --git a/encode_test.go b/encode_test.go
index 8f03d52..adb4e18 100644
--- a/encode_test.go
+++ b/encode_test.go
@@ -267,6 +267,38 @@ func TestEncoderUseLiteralMultilineThresholdZero(t *testing.T) {
 	}
 }
 
+func TestEncoderLiteralMultilineFallsBackWhenUnsafe(t *testing.T) {
+	// The literal form carries the value verbatim, so content it cannot
+	// represent must fall back to the escaped basic string instead of
+	// producing output that does not re-parse.
+	cases := []struct {
+		name string
+		in   string
+	}{
+		{"embedded delimiter", "before ''' after\nsecond line"},
+		{"control character", "a\x01b\nsecond"},
+		{"delete character", "a\x7fb\nsecond"},
+		{"lone carriage return", "first\rsecond\nthird"},
+	}
+	for _, c := range cases {
+		out, err := NewEncoder().UseLiteralMultiline(5).Marshal(map[string]any{"s": c.in})
+		if err != nil {
+			t.Fatalf("%s: marshal: %v", c.name, err)
+		}
+		if !bytes.HasPrefix(out, []byte("s = \"")) {
+			t.Errorf("%s: expected the basic quoted form, got:\n%s", c.name, out)
+		}
+		re, err := Parse(out)
+		if err != nil {
+			t.Errorf("%s: re-parse: %v\ndoc:\n%s", c.name, err, out)
+			continue
+		}
+		if re["s"] != c.in {
+			t.Errorf("%s: round-trip changed the value: %q", c.name, re["s"])
+		}
+	}
+}
+
 // marshalerFunc adapts a plain function value to the Marshaler interface.
 // Tests use it to express "this field produces this TOML value" without a
 // dedicated struct definition.