diff --git a/MacPass/EntryView.xib b/MacPass/EntryView.xib
index bc11ac8f..3a7e32e7 100644
--- a/MacPass/EntryView.xib
+++ b/MacPass/EntryView.xib
@@ -1,8 +1,8 @@
 <?xml version="1.0" encoding="UTF-8" standalone="no"?>
-<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="4514" systemVersion="13B42" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
+<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="5053" systemVersion="13C64" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
     <dependencies>
         <deployment defaultVersion="1080" identifier="macosx"/>
-        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="4514"/>
+        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="5053"/>
     </dependencies>
     <objects>
         <customObject id="-2" userLabel="File's Owner" customClass="MPEntryViewController">
@@ -48,11 +48,11 @@
                                         <tableColumnResizingMask key="resizingMask" resizeWithTable="YES" userResizable="YES"/>
                                         <prototypeCellViews>
                                             <tableCellView identifier="StringCell" id="269">
-                                                <rect key="frame" x="1" y="1" width="105" height="17"/>
+                                                <rect key="frame" x="1" y="1" width="104.5" height="17"/>
                                                 <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                                 <subviews>
                                                     <textField verticalHuggingPriority="750" horizontalCompressionResistancePriority="250" translatesAutoresizingMaskIntoConstraints="NO" id="270">
-                                                        <rect key="frame" x="1" y="0.0" width="103" height="17"/>
+                                                        <rect key="frame" x="1" y="0.0" width="102.5" height="17"/>
                                                         <autoresizingMask key="autoresizingMask" widthSizable="YES" flexibleMinY="YES"/>
                                                         <textFieldCell key="cell" lineBreakMode="truncatingTail" sendsActionOnEndEditing="YES" title="Table View Cell" id="271">
                                                             <font key="font" metaFont="system"/>
@@ -86,7 +86,7 @@
                                         <tableColumnResizingMask key="resizingMask" resizeWithTable="YES" userResizable="YES"/>
                                         <prototypeCellViews>
                                             <tableCellView identifier="ImageCell" id="297">
-                                                <rect key="frame" x="109" y="1" width="144" height="17"/>
+                                                <rect key="frame" x="108.5" y="1" width="144" height="17"/>
                                                 <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                                 <subviews>
                                                     <imageView translatesAutoresizingMaskIntoConstraints="NO" id="298">
@@ -94,6 +94,7 @@
                                                         <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
                                                         <constraints>
                                                             <constraint firstAttribute="width" constant="17" id="312"/>
+                                                            <constraint firstAttribute="height" constant="17" id="T73-FC-KyN"/>
                                                         </constraints>
                                                         <imageCell key="cell" refusesFirstResponder="YES" alignment="left" imageScaling="proportionallyDown" image="NSActionTemplate" id="301"/>
                                                     </imageView>
@@ -136,11 +137,11 @@
                                         <tableColumnResizingMask key="resizingMask" resizeWithTable="YES" userResizable="YES"/>
                                         <prototypeCellViews>
                                             <tableCellView identifier="PasswordCell" id="428">
-                                                <rect key="frame" x="256" y="1" width="119" height="17"/>
+                                                <rect key="frame" x="255.5" y="1" width="118.5" height="17"/>
                                                 <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                                 <subviews>
                                                     <textField verticalHuggingPriority="750" horizontalCompressionResistancePriority="250" translatesAutoresizingMaskIntoConstraints="NO" id="429" customClass="NSSecureTextField">
-                                                        <rect key="frame" x="1" y="0.0" width="117" height="17"/>
+                                                        <rect key="frame" x="1" y="0.0" width="116.5" height="17"/>
                                                         <autoresizingMask key="autoresizingMask" widthSizable="YES" flexibleMinY="YES"/>
                                                         <textFieldCell key="cell" lineBreakMode="truncatingTail" sendsActionOnEndEditing="YES" title="Table View Cell" id="430">
                                                             <font key="font" metaFont="system"/>
@@ -174,7 +175,7 @@
                                         <tableColumnResizingMask key="resizingMask" resizeWithTable="YES" userResizable="YES"/>
                                         <prototypeCellViews>
                                             <tableCellView id="421">
-                                                <rect key="frame" x="378" y="1" width="113" height="17"/>
+                                                <rect key="frame" x="377" y="1" width="113" height="17"/>
                                                 <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                                 <subviews>
                                                     <textField verticalHuggingPriority="750" horizontalCompressionResistancePriority="250" translatesAutoresizingMaskIntoConstraints="NO" id="422">
@@ -212,7 +213,7 @@
                                         <tableColumnResizingMask key="resizingMask" resizeWithTable="YES" userResizable="YES"/>
                                         <prototypeCellViews>
                                             <tableCellView id="616">
-                                                <rect key="frame" x="494" y="1" width="198" height="17"/>
+                                                <rect key="frame" x="493" y="1" width="198" height="17"/>
                                                 <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                                 <subviews>
                                                     <textField verticalHuggingPriority="750" horizontalCompressionResistancePriority="250" translatesAutoresizingMaskIntoConstraints="NO" id="617">
@@ -292,4 +293,4 @@
         <image name="NSActionTemplate" width="14" height="14"/>
         <image name="NSAddTemplate" width="8" height="8"/>
     </resources>
-</document>
\ No newline at end of file
+</document>
diff --git a/MacPass/KPKNode+IconImage.m b/MacPass/KPKNode+IconImage.m
index fbec8b84..08307a15 100644
--- a/MacPass/KPKNode+IconImage.m
+++ b/MacPass/KPKNode+IconImage.m
@@ -9,18 +9,26 @@
 #import "KPKNode+IconImage.h"
 
 #import "KPKIcon.h"
+#import "KPKGroup.h"
 #import "KPKTree.h"
 #import "KPKMetaData.h"
+#import "KPKTimeInfo.h"
 
 #import "MPIconHelper.h"
 
 @implementation KPKNode (IconImage)
 
 + (NSSet *)keyPathsForValuesAffectingIconImage {
-  return [NSSet setWithArray:@[@"iconUUID", @"iconId"]];
+  return [NSSet setWithArray:@[NSStringFromSelector(@selector(iconUUID)),
+                               NSStringFromSelector(@selector(iconId)),
+                               @"timeInfo.expires"]];
 }
 
 - (NSImage *)iconImage {
+  if(self.timeInfo.expires) {
+    const BOOL isGroup = [self isKindOfClass:[KPKGroup class]];
+    return [MPIconHelper icon:(isGroup ? MPIconExpiredGroup : MPIconExpiredEntry)];
+  }
   if(self.iconUUID) {
     KPKIcon *icon = [self.tree.metaData findIcon:self.iconUUID];
     if(icon && icon.image) {
diff --git a/MacPass/MPDocument.m b/MacPass/MPDocument.m
index 81a1310b..df30de22 100644
--- a/MacPass/MPDocument.m
+++ b/MacPass/MPDocument.m
@@ -171,6 +171,7 @@ NSString *const MPDocumentGroupKey                        = @"MPDocumentGroupKey
 }
 
 - (BOOL)readFromURL:(NSURL *)url ofType:(NSString *)typeName error:(NSError **)outError {
+  [self _watchForFileChanges:YES];
   /* FIXME: Lockfile handling
    self.lockFileURL = [url URLByAppendingPathExtension:@"lock"];
    if([[NSFileManager defaultManager] fileExistsAtPath:[_lockFileURL path]]) {
diff --git a/MacPass/MPIconHelper.h b/MacPass/MPIconHelper.h
index a4293728..c4f45ba2 100644
--- a/MacPass/MPIconHelper.h
+++ b/MacPass/MPIconHelper.h
@@ -48,6 +48,8 @@ typedef NS_ENUM(NSUInteger, MPIconType) {
   MPIconCreated,
   MPIconAddEntry,
   MPIconContextTriangle,
+  MPIconExpiredEntry,
+  MPIconExpiredGroup,
 };
 
 /**
diff --git a/MacPass/MPIconHelper.m b/MacPass/MPIconHelper.m
index eceaee22..c757e9cb 100644
--- a/MacPass/MPIconHelper.m
+++ b/MacPass/MPIconHelper.m
@@ -17,7 +17,8 @@
   }
   if([[icons allKeys] containsObject:@(type)]) {
     NSString *imageName = icons[@(type)];
-    return [[NSBundle mainBundle] imageForResource:imageName];
+    NSImage *image = [NSImage imageNamed:imageName];
+    return image;
   }
   return [NSImage imageNamed:NSImageNameActionTemplate];
 }
@@ -83,7 +84,10 @@
                    @(MPIconHardDisk): @"99_HarddiskTemplate",
                    @(MPIconCreated): @"99_CreatedTemplate",
                    @(MPIconAddEntry): @"addEntryTemplate",
-                   @(MPIconContextTriangle): @"contextTriangleTemplate"
+                   @(MPIconContextTriangle): @"contextTriangleTemplate",
+                   
+                   @(MPIconExpiredEntry): NSImageNameCaution,
+                   @(MPIconExpiredGroup): NSImageNameCaution
                    };
   });
   return imageNames;
diff --git a/MacPass/OutlineView.xib b/MacPass/OutlineView.xib
index 5ef0f11c..1de84ec2 100644
--- a/MacPass/OutlineView.xib
+++ b/MacPass/OutlineView.xib
@@ -1,8 +1,8 @@
 <?xml version="1.0" encoding="UTF-8" standalone="no"?>
-<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="4514" systemVersion="13A603" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
+<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="5053" systemVersion="13C64" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
     <dependencies>
         <deployment defaultVersion="1080" identifier="macosx"/>
-        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="4514"/>
+        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="5053"/>
     </dependencies>
     <objects>
         <customObject id="-2" userLabel="File's Owner" customClass="MPOutlineViewController">
@@ -78,8 +78,9 @@
                                                         <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
                                                         <constraints>
                                                             <constraint firstAttribute="width" constant="17" id="385"/>
+                                                            <constraint firstAttribute="height" constant="17" id="bah-Ng-60T"/>
                                                         </constraints>
-                                                        <imageCell key="cell" refusesFirstResponder="YES" alignment="left" image="NSActionTemplate" id="242"/>
+                                                        <imageCell key="cell" refusesFirstResponder="YES" alignment="left" imageScaling="proportionallyDown" image="NSActionTemplate" id="242"/>
                                                     </imageView>
                                                     <textField verticalHuggingPriority="750" translatesAutoresizingMaskIntoConstraints="NO" id="243" customClass="HNHBadgedTextField">
                                                         <rect key="frame" x="26" y="4" width="242" height="17"/>
@@ -158,4 +159,4 @@
         <image name="NSActionTemplate" width="14" height="14"/>
         <image name="NSAddTemplate" width="8" height="8"/>
     </resources>
-</document>
\ No newline at end of file
+</document>