diff --git a/libdash/printer.py b/libdash/printer.py
index 4317638..6c84f2a 100644
--- a/libdash/printer.py
+++ b/libdash/printer.py
@@ -408,14 +408,7 @@ def string_of_arg (args, quote_mode=UNQUOTED):
     text = []
     while i < len(args):
         c = string_of_arg_char(args[i], quote_mode=quote_mode)
-
-        # dash will parse '$?' as
-        # [(C, '$'), (E, '?')]
-        # but we don't normally want to escape ?
-        #
-        # so we check up after the fact: if the character after $ is escaped,
-        # we'll escape the $, too
-        if c == "$" and (i+1 < len(args)) and args[i+1][0] == "E":
+        if c == "$" and (i+1 < len(args)):
             c = "\\$"
         text.append(c)
 
diff --git a/ocaml/ast.ml b/ocaml/ast.ml
index 9205e83..80a77d4 100644
--- a/ocaml/ast.ml
+++ b/ocaml/ast.ml
@@ -468,7 +468,7 @@ and string_of_arg ?quote_mode:(quote_mode=QUnquoted) = function
   | [] -> ""
   | c :: a ->
      let char = string_of_arg_char ~quote_mode c in
-     if char = "$" && next_is_escaped a
+     if char = "$" && a <> []
      then "\\$" ^ string_of_arg ~quote_mode a
      else char ^ string_of_arg ~quote_mode a
 
diff --git a/test/round_trip.sh b/test/round_trip.sh
index 1fbc86b..df7c7af 100755
--- a/test/round_trip.sh
+++ b/test/round_trip.sh
@@ -8,6 +8,10 @@ fi
 p=$1
 tgt=$2
 
+two_roundtrips() {
+    [ "$(head -n1 "$tgt")" != '# TEST: single roundtrip' ]
+}
+
 orig=$(mktemp)
 
 "$p" "$tgt" >"$orig"
@@ -31,25 +35,31 @@ then
      echo "PASS '$tgt'"
      exit 0
 else
-    # try one more time around the loop
-    rtrt=$(mktemp)
-
-    "$p" "$rt" >"$rtrt"
-    if [ "$?" -ne 0 ]
+    if two_roundtrips
     then
-        echo "RT_ABORT_3: '$tgt' -> '$orig' -> '$rt' -> '$rtrt'"
-        exit 5
-    fi
+        # try one more time around the loop
+        rtrt=$(mktemp)
 
-    if diff -b "$rt" "$rtrt" >/dev/null
-    then
-        echo "PASS '$tgt' (two runs to fixpoint)"
-        exit 0
+        "$p" "$rt" >"$rtrt"
+        if [ "$?" -ne 0 ]
+        then
+            echo "RT_ABORT_3: '$tgt' -> '$orig' -> '$rt' -> '$rtrt'"
+            exit 5
+        fi
+
+        if diff -b "$rt" "$rtrt" >/dev/null
+        then
+            echo "PASS '$tgt' (two runs to fixpoint)"
+            exit 0
+        fi
     fi
-    
+
     echo "FAIL: '$tgt' first time"
     diff -ub "$orig" "$rt"
-    echo ">>> '$tgt' second time"
-    diff -ub "$rt" "$rtrt"
+    if two_roundtrips
+    then
+        echo ">>> '$tgt' second time"
+        diff -ub "$rt" "$rtrt"
+    fi
     exit 1
 fi
diff --git a/test/tests/single_quoted_dollar_sign.sh b/test/tests/single_quoted_dollar_sign.sh
new file mode 100644
index 0000000..53d1edc
--- /dev/null
+++ b/test/tests/single_quoted_dollar_sign.sh
@@ -0,0 +1,4 @@
+# TEST: single roundtrip
+
+echo '$1'
+echo $ a