diff --git a/MacPass/Base.lproj/IconSelection.xib b/MacPass/Base.lproj/IconSelection.xib
index 4c6c8d75..f0856904 100644
--- a/MacPass/Base.lproj/IconSelection.xib
+++ b/MacPass/Base.lproj/IconSelection.xib
@@ -1,12 +1,14 @@
 <?xml version="1.0" encoding="UTF-8"?>
-<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="12121" systemVersion="16G29" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
+<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="13196" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
     <dependencies>
-        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="12121"/>
+        <deployment identifier="macosx"/>
+        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="13196"/>
         <capability name="documents saved in the Xcode 8 format" minToolsVersion="8.0"/>
     </dependencies>
     <objects>
         <customObject id="-2" userLabel="File's Owner" customClass="MPIconSelectViewController">
             <connections>
+                <outlet property="downloadIconButton" destination="8kv-BJ-IEk" id="JH0-uV-F5k"/>
                 <outlet property="iconCollectionView" destination="58" id="77"/>
                 <outlet property="view" destination="1" id="56"/>
             </connections>
@@ -53,8 +55,8 @@
                     </connections>
                 </button>
                 <button verticalHuggingPriority="750" translatesAutoresizingMaskIntoConstraints="NO" id="8kv-BJ-IEk">
-                    <rect key="frame" x="153" y="18" width="104" height="25"/>
-                    <buttonCell key="cell" type="roundTextured" title="Download Icon" bezelStyle="texturedRounded" alignment="center" lineBreakMode="truncatingTail" state="on" borderStyle="border" imageScaling="proportionallyDown" inset="2" id="iaf-XW-XUo">
+                    <rect key="frame" x="149" y="18" width="108" height="25"/>
+                    <buttonCell key="cell" type="roundTextured" title="Download Icon" bezelStyle="texturedRounded" imagePosition="left" alignment="center" lineBreakMode="truncatingTail" state="on" borderStyle="border" imageScaling="proportionallyDown" inset="2" id="iaf-XW-XUo">
                         <behavior key="behavior" pushIn="YES" lightByBackground="YES" lightByGray="YES"/>
                         <font key="font" metaFont="system"/>
                     </buttonCell>
@@ -63,7 +65,7 @@
                     </connections>
                 </button>
                 <button verticalHuggingPriority="750" translatesAutoresizingMaskIntoConstraints="NO" id="His-4A-hcY">
-                    <rect key="frame" x="89" y="18" width="56" height="25"/>
+                    <rect key="frame" x="85" y="18" width="56" height="25"/>
                     <buttonCell key="cell" type="roundTextured" title="Cancel" bezelStyle="texturedRounded" alignment="center" state="on" borderStyle="border" imageScaling="proportionallyDown" inset="2" id="1kM-cI-P1o">
                         <behavior key="behavior" pushIn="YES" lightByBackground="YES" lightByGray="YES"/>
                         <font key="font" metaFont="system"/>
@@ -86,7 +88,7 @@
                 <constraint firstItem="57" firstAttribute="top" secondItem="1" secondAttribute="top" constant="20" symbolic="YES" id="iuz-pK-yXC"/>
                 <constraint firstItem="101" firstAttribute="leading" secondItem="8kv-BJ-IEk" secondAttribute="trailing" constant="8" symbolic="YES" id="nvi-CZ-a6L"/>
             </constraints>
-            <point key="canvasLocation" x="-143" y="15"/>
+            <point key="canvasLocation" x="-447" y="15"/>
         </customView>
         <collectionViewItem id="61" customClass="MPCollectionViewItem">
             <connections>
diff --git a/MacPass/MPIconSelectViewController.m b/MacPass/MPIconSelectViewController.m
index 84b3c027..0910a289 100644
--- a/MacPass/MPIconSelectViewController.m
+++ b/MacPass/MPIconSelectViewController.m
@@ -26,21 +26,33 @@
 #import "MPCollectionView.h"
 #import "MPCollectionViewItem.h"
 
+typedef NS_ENUM(NSInteger, MPIconDownloadStatus) {
+  MPIconDownloadStatusNone,
+  MPIconDownloadStatusProgress,
+  MPIconDownloadStatusError
+};
+
 @interface MPIconSelectViewController () <NSCollectionViewDelegate>
 
 /* UI properties */
 @property (weak) IBOutlet MPCollectionView *iconCollectionView;
 @property (weak) IBOutlet NSButton *imageButton;
+@property (weak) IBOutlet NSButton *downloadIconButton;
+@property (assign) MPIconDownloadStatus downloadStatus;
 
 @end
 
 @implementation MPIconSelectViewController
 
+@dynamic downloadStatus;
+
 - (NSString *)nibName {
   return @"IconSelection";
 }
 
 - (void)viewDidLoad {
+  KPKNode *node = self.representedObject;
+  self.downloadIconButton.enabled = (nil != node.asEntry);
   self.iconCollectionView.backgroundColors = @[NSColor.clearColor];
   self.iconCollectionView.selectable = YES;
   self.iconCollectionView.allowsMultipleSelection = NO;
@@ -64,35 +76,70 @@
 }
 
 - (IBAction)downloadIcon:(id)sender {
+  //self.downloadStatus = MPIconDownloadStatusProgress;
   KPKNode *node = self.representedObject;
   if(!node.asEntry) {
     return;
   }
-  NSString *rawURL = node.asEntry.url;
-  if([rawURL hasPrefix:@"http://"] || ![rawURL hasPrefix:@"https://"]) {
-    rawURL = [@"https://" stringByAppendingString:rawURL];
+  [self _downloadIconForURL:node.asEntry.url];
+}
+
+- (void)setDownloadStatus:(MPIconDownloadStatus)status {
+  switch (status) {
+    case MPIconDownloadStatusNone:
+      self.downloadIconButton.image = nil;
+      break;
+    case MPIconDownloadStatusError:
+      self.downloadIconButton.image = [NSImage imageNamed:NSImageNameCaution];
+      break;
+    case MPIconDownloadStatusProgress:
+      self.downloadIconButton.image = [NSImage imageNamed:NSImageNameRefreshTemplate];
+      break;
+  }
+}
+
+- (void)_downloadIconForURL:(NSString *)URLString {
+  if([URLString hasPrefix:@"http://"] || ![URLString hasPrefix:@"https://"]) {
+    URLString = [@"https://" stringByAppendingString:URLString];
   }
   
-  NSURL *url = [NSURL URLWithString:rawURL];
+  NSURL *url = [NSURL URLWithString:URLString];
   if(!url) {
+    self.downloadStatus = MPIconDownloadStatusError;
     return;
   }
   
   NSString *urlString = [NSString stringWithFormat:@"%@://%@/favicon.ico", url.scheme, url.host ? url.host : @""];
   NSURL *favIconURL = [NSURL URLWithString:urlString];
   if(!favIconURL) {
+    self.downloadStatus = MPIconDownloadStatusError;
     return;
   }
   
   KPKMetaData *metaData = ((MPDocument *)[NSDocumentController sharedDocumentController].currentDocument).tree.metaData;
   NSURLSessionTask *task = [[NSURLSession sharedSession] dataTaskWithURL:favIconURL completionHandler:^(NSData * _Nullable data, NSURLResponse * _Nullable response, NSError * _Nullable error) {
-    if(data) {
+    if(error) {
+      dispatch_async(dispatch_get_main_queue(), ^{
+        self.downloadStatus = MPIconDownloadStatusError;
+        [NSApp presentError:error];
+      });
+    }
+    if(data.length > 0) {
       dispatch_async(dispatch_get_main_queue(), ^{
         KPKIcon *newIcon = [[KPKIcon alloc] initWithImageData:data];
         if(newIcon) {
+          self.downloadStatus = MPIconDownloadStatusNone;
           [metaData addCustomIcon:newIcon];
           [self _updateCollectionViewContent];
         }
+        else {
+          self.downloadStatus = MPIconDownloadStatusError;
+        }
+      });
+    }
+    else {
+      dispatch_async(dispatch_get_main_queue(), ^{
+        self.downloadStatus = MPIconDownloadStatusError;
       });
     }
   }];
@@ -105,6 +152,9 @@
   if(index < firstCustomIndex) {
     return;
   }
+  if(index >= self.iconCollectionView.content.count) {
+    return;
+  }
   MPDocument *document = [NSDocumentController sharedDocumentController].currentDocument;
   KPKIcon *icon = self.iconCollectionView.content[index];
   [document.tree.metaData removeCustomIcon:icon];
@@ -127,6 +177,21 @@
   [self.view.window performClose:sender];
 }
 
+- (BOOL)validateMenuItem:(NSMenuItem *)menuItem {
+  if(menuItem.action == @selector(deleteIcon:)) {
+    NSUInteger index = self.iconCollectionView.contextMenuIndex;
+    NSUInteger firstCustomIndex = [MPIconHelper databaseIcons].count;
+    if(index < firstCustomIndex) {
+      return NO;
+    }
+    if(index >= self.iconCollectionView.content.count) {
+      return NO;
+    }
+    return YES;
+  }
+  return NO;
+}
+
 - (void)didSelectCollectionViewItem:(id)sender {
   if(![sender isKindOfClass:[NSCollectionViewItem class]]) {
     return;