diff --git a/config/punctuation/default.conf b/config/punctuation/default.conf
index e3995e53..9b5e1622 100644
--- a/config/punctuation/default.conf
+++ b/config/punctuation/default.conf
@@ -44,26 +44,31 @@ _:===:line
 =:===:equals
 
 [customDict]
+# This dictionary uses regexp, so be sure to escape anything that would be parsed by regexp, e.g. *, ., ^, $, etc.
 
 [emoticonDict]
-<{-.-}>:===:Raves
-8-):===:smile with sunglasses
-:-/:===:confused
--.-:===:bugged
->.<:===:laughing
-8-X:===:skull
->:):===:evil smile
->:-):===:evil smile
-\o/:===:Hurray
-:/:===:confused
-8):===:smile with sunglasses
-:D:===:laugh
-;):===:wink
-XD:===:LOL
-:-):===:smile
-:):===:smile
-->:===:arrow right
-<-:===:arrow left
-oO:===:WTF?
-Oo:===:WTF?
-^^:===:enjoy smile
+# This dictionary uses regexp, so be sure to escape anything that would be parsed by regexp, e.g. *, ., ^, $, etc.
+.*[\s*|'|"][\s*|'|"]<{-.-}>.*:===:Raves
+.*[\s*|'|"][\s*|'|"]8-\).*:===:smile with sunglasses
+.*[\s*|'|"][\s*|'|"]:-/.*:===:confused
+.*[\s*|'|"][\s*|'|"]-\.-.*:===:bugged
+.*[\s*|'|"][\s*|'|"]>\.<.*:===:laughing
+.*[\s*|'|"][\s*|'|"]8-X.*:===:skull
+.*[\s*|'|"][\s*|'|"]>:\).*:===:evil smile
+.*[\s*|'|"][\s*|'|"]>:-\).*:===:evil smile
+.*[\s*|'|"][\s*|'|"]\\o/.*:===:Hurray
+.*[\s*|'|"][\s*|'|"]:/.*:===:confused
+.*[\s*|'|"][\s*|'|"]8\).*:===:smile with sunglasses
+.*[\s*|'|"]:D[\s*|'|"].*:===:laugh
+.*[\s*|'|"];\)[\s*|'|"].*:===:wink
+.*[\s*|'|"]XD[\s*|'|"].*:===:LOL
+.*[\s*|'|"]:-\)[\s*|'|"].*:===:smile
+.*[\s*|'|"]:\)[\s*|'|"].*:===:smile
+.*[\s*|'|"]->[\s*|'|"].*:===:arrow right
+# example for arrow left
+#(?:[ |^])(<-)(?:[ ,.!?$]):===:arrow left
+# or
+#([ |^])<-([ ,.!?$]):===:arrow left\2
+.*[\s*|'|"]<-[\s*|'|"].*:===:arrow left
+.*[\s*|'|"][O|o][O|o][\s*|'|"].*:===:WTF?
+.*[\s*|'|"]\^\^[\s*|'|"].*:===:enjoy smile
diff --git a/src/fenrirscreenreader/core/punctuationManager.py b/src/fenrirscreenreader/core/punctuationManager.py
index a98577ea..767d62ae 100644
--- a/src/fenrirscreenreader/core/punctuationManager.py
+++ b/src/fenrirscreenreader/core/punctuationManager.py
@@ -33,15 +33,16 @@ class punctuationManager():
                 del currAllPunctNone[ord(char)]
             except:
                 pass
-        return text.translate(currAllPunctNone)   
-    
+        return text.translate(currAllPunctNone)
     def useCustomDict(self, text, customDict, seperator=''):
         resultText = str(text)
         if customDict:
             for key,item in customDict.items():
-                resultText = resultText.replace(str(key),seperator + str(item) + seperator)
+                try:
+                    resultText = re.sub(str(key), seperator + str(item) + seperator, resultText)
+                except:
+                    resultText = resultText.replace(str(key),seperator + str(item) + seperator)
         return resultText
-    
     def usePunctuationDict(self, text, punctuationDict, punctuation):
         resultText = str(text)
 
@@ -53,7 +54,7 @@ class punctuationManager():
                     if self.env['runtime']['settingsManager'].getSetting('general', 'respectPunctuationPause') and \
                       len(key) == 1 and \
                       key in "',.;:?!":
-                        resultText = resultText.replace(str(key),' ' +str(item) + str(key) + ' ')                    
+                        resultText = resultText.replace(str(key),' ' +str(item) + str(key) + ' ')
                     else:
                         resultText = resultText.replace(str(key),' ' +str(item) + ' ')
         return resultText