diff --git a/src/calibre/ebooks/textile/functions.py b/src/calibre/ebooks/textile/functions.py
index 88d27b036d..c3c82ef893 100755
--- a/src/calibre/ebooks/textile/functions.py
+++ b/src/calibre/ebooks/textile/functions.py
@@ -211,16 +211,6 @@ class Textile(object):
         (re.compile(r'(\d+\'?\"?)( ?)x( ?)(?=\d+)'),                   r'\1\2×\3'),                       #  dimension sign
         (re.compile(r'(\d+)\'', re.I),                                 r'\1′'),                          #  prime
         (re.compile(r'(\d+)\"', re.I),                                 r'\1″'),                          #  prime-double
-        (re.compile(r'(\')\''),                                        r'\1’'),                          #  single closing - following another
-        (re.compile(r"(\w)\'(\w)"),                                    r'\1’\2'),                        #  apostrophe's
-        (re.compile(r'(\s)\'(\d+\w?)\b(?!\')'),                        r'\1’\2'),                        #  back in '88
-        (re.compile(r'(\s\[)\''),                                      r'\1‘'),                          #  single opening - following ws+[
-        (re.compile(r'(\S)\'(?=\s|'+pnct+'|<|$)', re.M),               r'\1&#8217;'),                          #  single closing
-        (re.compile(r'\''),                                            r'&#8216;'),                            #  single opening
-        (re.compile(r'(\")\"'),                                        r'\1&#8221;'),                          #  double closing - following another
-        (re.compile(r'(\s\[)\"'),                                      r'\1&#8220;'),                          #  double opening - following whitespace+[
-        (re.compile(r'(\S)\"(?=\s|'+pnct+'|<|$)', re.M),               r'\1&#8221;'),                          #  double closing
-        (re.compile(r'"'),                                             r'&#8220;'),                            #  double opening
         (re.compile(r'\b([A-Z][A-Z0-9]{2,})\b(?:[(]([^)]*)[)])'),      r'<acronym title="\2">\1</acronym>'),   #  3+ uppercase acronym
         (re.compile(r'\b([A-Z][A-Z\'\-]+[A-Z])(?=[\s.,\)>])'),         r'<span class="caps">\1</span>'),       #  3+ uppercase
         (re.compile(r'\b(\s{0,1})?\.{3}'),                             r'\1&#8230;'),                          #  ellipsis
@@ -870,11 +860,11 @@ class Textile(object):
         'hello <span class="bob">span <strong>strong</strong> and <b>bold</b></span> goodbye'
         """
         qtags = (r'\*\*', r'\*', r'\?\?', r'\-', r'__', r'_', r'%', r'\+', r'~', r'\^')
-        pnct = ".,\"'?!;:()"
+        pnct = ".,\"'?!;:"
 
         for qtag in qtags:
             pattern = re.compile(r"""
-                (?:^|(?<=[\s>%(pnct)s])|\[|([\]}]))
+                (?:^|(?<=[\s>%(pnct)s\(])|\[|([\]}]))
                 (%(qtag)s)(?!%(qtag)s)
                 (%(c)s)
                 (?::(\S+))?
diff --git a/src/calibre/ebooks/txt/input.py b/src/calibre/ebooks/txt/input.py
index 99f7035800..7face4c24f 100644
--- a/src/calibre/ebooks/txt/input.py
+++ b/src/calibre/ebooks/txt/input.py
@@ -165,6 +165,7 @@ class TXTInput(InputFormatPlugin):
         elif options.formatting_type == 'textile':
             log.debug('Running text through textile conversion...')
             html = convert_textile(txt)
+            setattr(options, 'smarten_punctuation', True)
         else:
             log.debug('Running text through basic conversion...')
             flow_size = getattr(options, 'flow_size', 0)
diff --git a/src/calibre/utils/smartypants.py b/src/calibre/utils/smartypants.py
index 62845b8d7a..8763a313fc 100644
--- a/src/calibre/utils/smartypants.py
+++ b/src/calibre/utils/smartypants.py
@@ -584,6 +584,12 @@ def educateQuotes(str):
 	#   <p>He said, "'Quoted' words in a larger quote."</p>
 	str = re.sub(r""""'(?=\w)""", """&#8220;&#8216;""", str)
 	str = re.sub(r"""'"(?=\w)""", """&#8216;&#8220;""", str)
+	str = re.sub(r'''""(?=\w)''', """&#8220;&#8220;""", str)
+	str = re.sub(r"""''(?=\w)""", """&#8216;&#8216;""", str)
+	str = re.sub(r'''\"\'''',     """&#8221;&#8217;""", str)
+	str = re.sub(r'''\'\"''',     """&#8217;&#8221;""", str)
+	str = re.sub(r'''""''',       """&#8221;&#8221;""", str)
+	str = re.sub(r"""''""",       """&#8217;&#8217;""", str)
 
 	# Special case for decade abbreviations (the '80s):
 	str = re.sub(r"""\b'(?=\d{2}s)""", r"""&#8217;""", str)