diff --git a/MacPass/MPAutotypeCommand.m b/MacPass/MPAutotypeCommand.m
index f4357e91..1d531a59 100644
--- a/MacPass/MPAutotypeCommand.m
+++ b/MacPass/MPAutotypeCommand.m
@@ -20,6 +20,24 @@
 
 #import <Carbon/Carbon.h>
 
+@interface NSNumber (AutotypeCommand)
+
+- (CGEventFlags)eventFlagsValue;
+- (CGKeyCode)keyCodeValue;
+
+@end
+
+@implementation NSNumber (AutotypeCommand)
+
+- (CGEventFlags)eventFlagsValue {
+  return (CGEventFlags)[self integerValue];
+}
+- (CGKeyCode)keyCodeValue {
+  return (CGKeyCode)[self integerValue];
+}
+
+@end
+
 @implementation MPAutotypeCommand
 
 + (NSDictionary *)keypressCommands {
@@ -57,7 +75,7 @@
 
 /**
  *  Mapping for modifier to CGEventFlags.
- *  @note KeypassControl is mapped to command!
+ *  @note KeepassControl is mapped to command!
  *
  *  @return dictionary with commands as keys and CGEventFlags as wrapped values
  */
@@ -83,7 +101,7 @@
   NSMutableArray __block *commandRanges = [[NSMutableArray alloc] initWithCapacity:reserverd];
   NSRegularExpression *commandRegExp = [[NSRegularExpression alloc] initWithPattern:@"\\{[^\\}]+\\}" options:NSRegularExpressionCaseInsensitive error:0];
   NSAssert(commandRegExp, @"RegExp is constant. Has to work all the time");
-  [commandRegExp enumerateMatchesInString:context.normalizedCommand options:0 range:NSMakeRange(0, [context.normalizedCommand length]) usingBlock:^(NSTextCheckingResult *result, NSMatchingFlags flags, BOOL *stop) {
+  [commandRegExp enumerateMatchesInString:context.evaluatedCommand options:0 range:NSMakeRange(0, [context.evaluatedCommand length]) usingBlock:^(NSTextCheckingResult *result, NSMatchingFlags flags, BOOL *stop) {
     @autoreleasepool {
       [commandRanges addObject:[NSValue valueWithRange:result.range]];
     }
@@ -94,16 +112,17 @@
     NSRange commandRange = [rangeValue rangeValue];
     /* All non-commands will get translated into paste commands */
     if(commandRange.location > lastLocation) {
-      /* If were modifiers we need to use the next single stroke and make update the modifier command */
+      /* If there were modifiers we need to use the next single stroke and make update the modifier command */
       if(keyPress) {
+        
       }
-      NSString *pasteValue = [context.normalizedCommand substringWithRange:NSMakeRange(lastLocation, commandRange.location - lastLocation)];
+      NSString *pasteValue = [context.evaluatedCommand substringWithRange:NSMakeRange(lastLocation, commandRange.location - lastLocation)];
       // Determin if it's amodifier key, and collect them!
       [self appendPasteCommandForContent:pasteValue toCommands:commands];
     }
-    NSString *commandString = [context.normalizedCommand substringWithRange:commandRange];
-    [self appendCommandForString:commandString toCommands:commands];
-    lastLocation = commandRange.location;
+    NSString *commandString = [context.evaluatedCommand substringWithRange:commandRange];
+    [self appendCommandForString:commandString toCommands:commands keyPressCommand:&keyPress];
+    lastLocation = commandRange.location + commandRange.length;
   }
   return commands;
 }
@@ -115,10 +134,41 @@
   }
 }
 
-+ (void)appendCommandForString:(NSString *)commandString toCommands:(NSMutableArray *)commands {
-  MPAutotypeCommand *command;
++ (void)appendCommandForString:(NSString *)commandString toCommands:(NSMutableArray *)commands keyPressCommand:(MPAutotypeKeyPress **)keyPress {
   if(!commandString) {
-    NSDictionary *modifier = [self modifierCommands];
+    return;
+  }
+  
+  NSNumber *flagNumber = [self modifierCommands][commandString];
+  NSNumber *keyCodeNumber = [self keypressCommands][commandString];
+  
+  /* modifier key */
+  if(flagNumber) {
+    if(keyPress == NULL) {
+      return; // We need a pointer to return the keypress!
+    }
+    CGEventFlags flags = [flagNumber eventFlagsValue];
+    if(*keyPress == nil) {
+      *keyPress = [[MPAutotypeKeyPress alloc] initWithModifierMask:flags keyCode:0];
+      [commands addObject:*keyPress];
+    }
+    else {
+      NSAssert([*keyPress isKindOfClass:[MPAutotypeKeyPress class]], @"Invalid command supplied");
+      (*keyPress).modifierMask |= flags;
+    }
+  }
+  /* key press */
+  else if(keyCodeNumber) {
+    CGKeyCode keyCode = [keyCodeNumber keyCodeValue];
+    /* we have no modifers collected */
+    if(keyPress != NULL && keyPress == nil) {
+      *keyPress = [[MPAutotypeKeyPress alloc] initWithModifierMask:0 keyCode:keyCode];
+      [commands addObject:*keyPress];
+    }
+    /* modifers collected, set keycode */
+    else if(keyPress) {
+      (*keyPress).keyCode = keyCode;
+    }
   }
 }
 
diff --git a/MacPass/MPAutotypeContext.h b/MacPass/MPAutotypeContext.h
index 7b7a5097..d83cfd73 100644
--- a/MacPass/MPAutotypeContext.h
+++ b/MacPass/MPAutotypeContext.h
@@ -26,6 +26,10 @@
  */
 @property (nonatomic, readonly, copy) NSString *command;
 @property (nonatomic, readonly, copy) NSString *normalizedCommand;
+/**
+ *  Command with placeholders and references resolved
+ */
+@property (nonatomic, readonly, copy) NSString *evaluatedCommand;
 
 /**
  *  Designated initializer
@@ -45,6 +49,4 @@
  */
 - (BOOL)isValid;
 
-- (NSString *)evaluatedCommand;
-
 @end
diff --git a/MacPass/MPAutotypeContext.m b/MacPass/MPAutotypeContext.m
index f1ceca3a..fb7b12e6 100644
--- a/MacPass/MPAutotypeContext.m
+++ b/MacPass/MPAutotypeContext.m
@@ -13,6 +13,12 @@
 #import "KPKWindowAssociation.h"
 #import "NSString+Commands.h"
 
+@interface MPAutotypeContext () {
+  NSString *_evaluatedCommand;
+}
+
+@end
+
 @implementation MPAutotypeContext
 
 - (instancetype)initWithWindowAssociation:(KPKWindowAssociation *)association {
@@ -46,12 +52,11 @@
 }
 
 - (NSString *)evaluatedCommand {
-  static NSString *evaluated;
-  if(!evaluated) {
+  if(!_evaluatedCommand) {
     NSString *placeholderFilled = [self.normalizedCommand evaluatePlaceholderWithEntry:self.entry];
-    evaluated = [placeholderFilled resolveReferencesWithTree:self.entry.tree];
+    _evaluatedCommand = [[placeholderFilled resolveReferencesWithTree:self.entry.tree] copy];
   }
-  return evaluated;
+  return _evaluatedCommand;
 }
 
 @end
diff --git a/MacPass/MPAutotypeDaemon.m b/MacPass/MPAutotypeDaemon.m
index a212615e..5f496d3e 100644
--- a/MacPass/MPAutotypeDaemon.m
+++ b/MacPass/MPAutotypeDaemon.m
@@ -65,7 +65,6 @@ NSString *const kMPApplciationNameKey = @"applicationName";
   NSMenuItem *item = [self.matchSelectionButton selectedItem];
   MPAutotypeContext *context = [item representedObject];
   [self.matchSelectionWindow orderOut:self];
-  
 }
 
 - (void)_didPressHotKey {
diff --git a/MacPass/MPAutotypeKeyPress.h b/MacPass/MPAutotypeKeyPress.h
index 4cd99b0a..f8b7ad61 100644
--- a/MacPass/MPAutotypeKeyPress.h
+++ b/MacPass/MPAutotypeKeyPress.h
@@ -16,4 +16,6 @@
 @property (assign) CGEventFlags modifierMask;
 @property (assign) CGKeyCode keyCode;
 
+- (instancetype)initWithModifierMask:(CGEventFlags)modiferMask keyCode:(CGKeyCode)code;
+
 @end
diff --git a/MacPass/MPAutotypeKeyPress.m b/MacPass/MPAutotypeKeyPress.m
index 5f0fe8fc..c12687b9 100644
--- a/MacPass/MPAutotypeKeyPress.m
+++ b/MacPass/MPAutotypeKeyPress.m
@@ -11,6 +11,15 @@
 
 @implementation MPAutotypeKeyPress
 
+- (instancetype)initWithModifierMask:(CGEventFlags)modiferMask keyCode:(CGKeyCode)code {
+  self = [super init];
+  if(self) {
+    _modifierMask = modiferMask;
+    _keyCode = code;
+  }
+  return self;
+}
+
 - (void)execute {
   if(![self isValid]) {
     return; // no valid command. Stop.