diff --git a/tests/test_lexer.py b/tests/test_lexer.py
index 90b678826..e44d0829d 100644
--- a/tests/test_lexer.py
+++ b/tests/test_lexer.py
@@ -192,6 +192,11 @@ def test_single_bytes_literal():
 def test_path_string_literal():
     assert check_token("p'/foo'", ['STRING', "p'/foo'", 0])
     assert check_token('p"/foo"', ['STRING', 'p"/foo"', 0])
+    assert check_token("pr'/foo'", ['STRING', "pr'/foo'", 0])
+    assert check_token('pr"/foo"', ['STRING', 'pr"/foo"', 0])
+    assert check_token("rp'/foo'", ['STRING', "rp'/foo'", 0])
+    assert check_token('rp"/foo"', ['STRING', 'rp"/foo"', 0])
+
 
 def test_regex_globs():
     for i in ('.*', r'\d*', '.*#{1,2}'):
diff --git a/tests/test_parser.py b/tests/test_parser.py
index 6f69e22ef..81b9f8743 100644
--- a/tests/test_parser.py
+++ b/tests/test_parser.py
@@ -1492,6 +1492,10 @@ def test_async_await():
 
 def test_path_literal():
     check_xonsh_ast({}, 'p"/foo"', False)
+    check_xonsh_ast({}, 'pr"/foo"', False)
+    check_xonsh_ast({}, 'rp"/foo"', False)
+    check_xonsh_ast({}, 'pR"/foo"', False)
+    check_xonsh_ast({}, 'Rp"/foo"', False)
 
 def test_dollar_name():
     check_xonsh_ast({'WAKKA': 42}, '$WAKKA')
diff --git a/xonsh/parsers/base.py b/xonsh/parsers/base.py
index 2c95e6d0d..085f8b8f3 100644
--- a/xonsh/parsers/base.py
+++ b/xonsh/parsers/base.py
@@ -16,12 +16,14 @@ from xonsh import ast
 from xonsh.ast import has_elts, xonsh_call
 from xonsh.lexer import Lexer, LexToken
 from xonsh.platform import PYTHON_VERSION_INFO
-from xonsh.tokenize import SearchPath
+from xonsh.tokenize import SearchPath, StringPrefix
 from xonsh.lazyasd import LazyObject
 from xonsh.parsers.context_check import check_contexts
 
 RE_SEARCHPATH = LazyObject(lambda: re.compile(SearchPath), globals(),
                            'RE_SEARCHPATH')
+RE_STRINGPREFIX = LazyObject(lambda: re.compile(StringPrefix), globals(),
+                             'RE_STRINGPREFIX')
 
 
 class Location(object):
@@ -1977,14 +1979,16 @@ class BaseParser(object):
     def p_string_literal(self, p):
         """string_literal : string_tok"""
         p1 = p[1]
-        if p1.value.startswith('p'):
-            s = ast.Str(s=ast.literal_eval(p1.value[1:]), lineno=p1.lineno,
+        prefix = RE_STRINGPREFIX.match(p1.value).group()
+        if 'p' in prefix:
+            value_without_p = prefix.replace('p', '') + p1.value[len(prefix):]
+            s = ast.Str(s=ast.literal_eval(value_without_p), lineno=p1.lineno,
                         col_offset=p1.lexpos)
             p[0] = xonsh_call('__xonsh_path_literal__', [s],
                               lineno=p1.lineno, col=p1.lexpos)
         else:
             s = ast.literal_eval(p1.value)
-            cls = ast.Bytes if p1.value.startswith('b') else ast.Str
+            cls = ast.Bytes if 'b' in prefix else ast.Str
             p[0] = cls(s=s, lineno=p1.lineno, col_offset=p1.lexpos)
 
     def p_string_literal_list(self, p):
diff --git a/xonsh/tokenize.py b/xonsh/tokenize.py
index 4b1837522..3d4b5d92e 100644
--- a/xonsh/tokenize.py
+++ b/xonsh/tokenize.py
@@ -205,7 +205,7 @@ Floatnumber = group(Pointfloat, Expfloat)
 Imagnumber = group(r'[0-9]+[jJ]', Floatnumber + r'[jJ]')
 Number = group(Imagnumber, Floatnumber, Intnumber)
 
-StringPrefix = r'(?:[bB][rR]?|[rR][bB]?|[uU]|[p])?'
+StringPrefix = r'(?:[bBp][rR]?|[rR][bBp]?|[uU])?'
 
 # Tail end of ' string.
 Single = r"[^'\\]*(?:\\.[^'\\]*)*'"
@@ -276,6 +276,10 @@ endpats = {"'": Single, '"': Double,
            "u'''": Single3, 'u"""': Double3,
            "U'''": Single3, 'U"""': Double3,
            "p'''": Single3, 'p"""': Double3,
+           "pr'''": Single3, 'pr"""': Double3,
+           "pR'''": Single3, 'pR"""': Double3,
+           "rp'''": Single3, 'rp"""': Double3,
+           "Rp'''": Single3, 'Rp"""': Double3,
            'r': None, 'R': None, 'b': None, 'B': None,
            'u': None, 'U': None, 'p': None}
 
@@ -288,7 +292,9 @@ for t in ("'''", '"""',
           "rb'''", 'rb"""', "rB'''", 'rB"""',
           "Rb'''", 'Rb"""', "RB'''", 'RB"""',
           "u'''", 'u"""', "U'''", 'U"""',
-          "p'''", 'p""""',
+          "p'''", 'p""""', "pr'''", 'pr""""',
+          "pR'''", 'pR""""', "rp'''", 'rp""""',
+          "Rp'''", 'Rp""""',
           ):
     triple_quoted[t] = t
 single_quoted = {}
@@ -300,7 +306,9 @@ for t in ("'", '"',
           "rb'", 'rb"', "rB'", 'rB"',
           "Rb'", 'Rb"', "RB'", 'RB"',
           "u'", 'u"', "U'", 'U"',
-          "p'", 'p"',
+          "p'", 'p"', "pr'", 'pr"',
+          "pR'", 'pR"', "rp'", 'rp"',
+          "Rp'", 'Rp"',
           ):
     single_quoted[t] = t