diff --git a/config/punctuation/de.conf b/config/punctuation/de.conf
index 7e63dfc6..81f33903 100644
--- a/config/punctuation/de.conf
+++ b/config/punctuation/de.conf
@@ -44,10 +44,29 @@ _:===:Lienie unten
 =:===:Istgleich
 
 [customDict]
-
 [emoticonDict]
-:):===:Grins
-;):===:Zwinker
-XD:===:loool
-:D:===:Lach
-<{-.-}>:===:Raves
+# 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/config/punctuation/default.conf b/config/punctuation/default.conf
index e3995e53..22cdc00e 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/config/punctuation/en.conf b/config/punctuation/en.conf
index 21e51c02..005a7bb7 100644
--- a/config/punctuation/en.conf
+++ b/config/punctuation/en.conf
@@ -44,10 +44,29 @@ _:===:line
 =:===:equals
 
 [customDict]
-
 [emoticonDict]
-:):===:smile
-;):===:twinker
-XD:===:loool
-:D:===:lought
-<{-.-}>:===:Raves
+# 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/config/punctuation/es.conf b/config/punctuation/es.conf
index f95d3c73..8bfe9612 100644
--- a/config/punctuation/es.conf
+++ b/config/punctuation/es.conf
@@ -44,10 +44,29 @@ _:===:subrayado
 =:===:igual
 
 [customDict]
-
 [emoticonDict]
-:):===:sonrisa
-;):===:twinker
-XD:===:loool
-:D:===:lought
-<{-.-}>:===:Raves
+# 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/config/punctuation/fr.conf b/config/punctuation/fr.conf
index ff36dffd..475db2be 100644
--- a/config/punctuation/fr.conf
+++ b/config/punctuation/fr.conf
@@ -44,10 +44,29 @@ _:===:souligné
 =:===:égale à
 
 [customDict]
-
 [emoticonDict]
-:):===:sourire
-;):===:clin d'oeil
-XD:===:explosé de rire
-:D:===:rire
-<{-.-}>:===:Raves
+# 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/config/punctuation/pl.conf b/config/punctuation/pl.conf
index 59356403..75152d0c 100644
--- a/config/punctuation/pl.conf
+++ b/config/punctuation/pl.conf
@@ -44,10 +44,29 @@ _:===:podkreślnik
 =:===:równa się
 
 [customDict]
-
 [emoticonDict]
-:):===:smile
-;):===:twinker
-XD:===:loool
-:D:===:lought
-<{-.-}>:===:Raves
+# 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..57416204 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)
 
@@ -49,11 +50,11 @@ class punctuationManager():
             if ' ' in punctuation:
                 resultText = resultText.replace(' ',' ' + punctuationDict[' '] + ' ')
             for key,item in punctuationDict.items():
-                if key in punctuation and key not in ' ':
+                if (punctuation != '' and key in punctuation) and key not in ' ':
                     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