diff --git a/spacy/tests/website/test_api.py b/spacy/tests/website/test_api.py
index fc5eb3c7a..6a7379d87 100644
--- a/spacy/tests/website/test_api.py
+++ b/spacy/tests/website/test_api.py
@@ -150,7 +150,7 @@ def test_example_i_like_new_york5(toks, autumn, dot):
     assert toks[autumn].head.orth_ == 'in'
     assert toks[dot].head.orth_ == 'like'
     autumn_dot = toks[autumn:]
-    assert autumn_dot.root.orth_ == '.'
+    assert autumn_dot.root.orth_ == 'Autumn'
 
 
 def test_navigating_the_parse_tree_lefts(doc):
diff --git a/spacy/tokens/span.pyx b/spacy/tokens/span.pyx
index 82501dbc5..801c98523 100644
--- a/spacy/tokens/span.pyx
+++ b/spacy/tokens/span.pyx
@@ -241,6 +241,12 @@ cdef class Span:
 
 
 cdef int _count_words_to_root(const TokenC* token, int sent_length) except -1:
+    # Don't allow spaces to be the root, if there are
+    # better candidates
+    if Lexeme.c_check_flag(token.lex, IS_SPACE) and token.l_kids == 0 and token.r_kids == 0:
+        return sent_length-1
+    if Lexeme.c_check_flag(token.lex, IS_PUNCT) and token.l_kids == 0 and token.r_kids == 0:
+        return sent_length-1
     cdef int n = 0
     while token.head != 0:
         token += token.head