diff --git a/.DS_Store b/.DS_Store
index 460f90099a3061137ffce657c135e70ea814b905..03e5283108dec403316b84b08663f92109f4ac7a 100644
Binary files a/.DS_Store and b/.DS_Store differ
diff --git a/Screenshottr/AppDelegate.swift b/Screenshottr/AppDelegate.swift
index 487abe911bc33a108fab393c315c95b263997d15..81c1d3f746aaa9a04f67a6696c7aebc6a6eba73b 100644
--- a/Screenshottr/AppDelegate.swift
+++ b/Screenshottr/AppDelegate.swift
@@ -13,8 +13,7 @@ import SKQueue
 class AppDelegate: NSObject, NSApplicationDelegate {
     let statusItem = NSStatusBar.system.statusItem(withLength: NSStatusItem.variableLength)
     let popover = NSPopover()
-    let viewController = PopoverMenu(nibName: "PopoverMenu",
-                                     bundle: Bundle.main)
+    let viewController = PopoverMenu(nibName: "PopoverMenu", bundle: Bundle.main)
     let statusIcon = NSImage(named: "status_icon")
     var spinnerView = NSView()
     let spinner = NSProgressIndicator()
diff --git a/Screenshottr/DropView.swift b/Screenshottr/DropView.swift
index f764af1ff49dc267d6701add670512d52f6eef46..cdeb0f16c6276cd7606641192cc441146e335d6d 100644
--- a/Screenshottr/DropView.swift
+++ b/Screenshottr/DropView.swift
@@ -8,38 +8,28 @@
 
 import Cocoa
 
-class DropView: NSImageView {
-    @IBOutlet var uploadImage: DropView!
-    @IBOutlet var textLabel: NSTextField!
-
-    var filePath: String?
+class DropView: NSView {
+	@IBOutlet weak var textLabel: NSTextField! //FIXME: Value is Nil despite outlet existing. https://stackoverflow.com/questions/58314461/outlet-definition-is-nil-despite-outlet-existing
+	var filePath: String?
 
     required init?(coder: NSCoder) {
         super.init(coder: coder)
-        isEditable = false
+        //isEditable = false
         wantsLayer = true
         registerForDraggedTypes([NSPasteboard.PasteboardType.URL, NSPasteboard.PasteboardType.fileURL])
     }
 
     override func draggingEntered(_: NSDraggingInfo) -> NSDragOperation {
-        textLabel.stringValue = "*notices your file* owo what's this?"
+        //textLabel.stringValue = "*notices your file* owo what's this?"
         return .copy
     }
 
     override func draggingEnded(_: NSDraggingInfo) {
-        textLabel.stringValue = "Drag and Drop to Upload"
-        image = NSImage(named: "upload")
-        /*
-         * For anybody in the future: The reason we change the image is because, for some reason, the
-         * image view in PopoverMenu will not connect to the outlet, meaning I cannot mark it as un-editable.
-         * No matter how hard I try it is an editable image view.
-         * If you, future person, find a solution, please email me. My email will be on https://github.com/broman
-         * But I am currently reachable at ryan@broman.dev
-         */
+        //textLabel.stringValue = "Drag and Drop to Upload"
     }
 
     override func draggingExited(_: NSDraggingInfo?) {
-        textLabel.stringValue = "Drag and Drop to Upload"
+        //textLabel.stringValue = "Drag and Drop to Upload"
     }
 
     override func performDragOperation(_ sender: NSDraggingInfo) -> Bool {
diff --git a/Screenshottr/DropViewController.swift b/Screenshottr/DropViewController.swift
new file mode 100644
index 0000000000000000000000000000000000000000..af7000730d5a190ff79e2f2b9e75eb2f654b3d10
--- /dev/null
+++ b/Screenshottr/DropViewController.swift
@@ -0,0 +1,13 @@
+//
+//  DropViewController.swift
+//  Screenshottr
+//
+//  Created by Ryan Broman on 26/09/19.
+//  Copyright © 2019 JOS Computing. All rights reserved.
+//
+
+import Cocoa
+
+class DropViewController {
+	@IBOutlet weak var uploaderImage: DropView!
+}
diff --git a/Screenshottr/PopoverMenu.swift b/Screenshottr/PopoverMenu.swift
index 8e230d1d667271b06cf0fec8706043720ad7abaa..4533ba77c87d76b72a010206823a0afde6da7399 100644
--- a/Screenshottr/PopoverMenu.swift
+++ b/Screenshottr/PopoverMenu.swift
@@ -9,11 +9,14 @@
 import Cocoa
 
 class PopoverMenu: NSViewController {
-    let settingsMenu = NSMenu()
+	@IBOutlet weak var uploadButton: NSButton!
+	
+	let settingsMenu = NSMenu()
 
     override func viewDidLoad() {
         super.viewDidLoad()
         // Do view setup here.
+		uploadButton.isHighlighted = false
         let settingsItem = NSMenuItem()
         settingsItem.action = #selector(presentSettingsDialog)
         settingsItem.title = "Settings"
diff --git a/Screenshottr/PopoverMenu.xib b/Screenshottr/PopoverMenu.xib
index 1ca9b7a9e4f32c5258a84e0d679d27675d0c18fb..0eb81179bb11f845e941ed8dfbdbfef5c77e0e9f 100644
--- a/Screenshottr/PopoverMenu.xib
+++ b/Screenshottr/PopoverMenu.xib
@@ -7,13 +7,14 @@
     <objects>
         <customObject id="-2" userLabel="File's Owner" customClass="PopoverMenu" customModule="Screenshottr" customModuleProvider="target">
             <connections>
+                <outlet property="uploadButton" destination="jrN-oy-XGI" id="wjX-1I-3Py"/>
                 <outlet property="view" destination="Hz6-mo-xeY" id="0bl-1N-x8E"/>
             </connections>
         </customObject>
         <customObject id="-1" userLabel="First Responder" customClass="FirstResponder"/>
         <customObject id="-3" userLabel="Application" customClass="DropView">
             <connections>
-                <outlet property="uploadImage" destination="687-0U-0uf" id="lti-id-9I9"/>
+                <outlet property="textLabel" destination="fj4-kJ-fXa" id="Fz7-VA-xTL"/>
             </connections>
         </customObject>
         <customView id="Hz6-mo-xeY">
@@ -21,7 +22,7 @@
             <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
             <subviews>
                 <button verticalHuggingPriority="750" fixedFrame="YES" translatesAutoresizingMaskIntoConstraints="NO" id="jrN-oy-XGI">
-                    <rect key="frame" x="78" y="13" width="108" height="32"/>
+                    <rect key="frame" x="72" y="6" width="120" height="43"/>
                     <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
                     <buttonCell key="cell" type="push" title="Upload File" bezelStyle="rounded" alignment="center" borderStyle="border" imageScaling="proportionallyDown" inset="2" id="7jj-A4-JC3">
                         <behavior key="behavior" pushIn="YES" lightByBackground="YES" lightByGray="YES"/>
@@ -31,8 +32,28 @@
                         <action selector="uploadFileClicked:" target="-2" id="jft-g4-t1c"/>
                     </connections>
                 </button>
+                <imageView horizontalHuggingPriority="251" verticalHuggingPriority="251" fixedFrame="YES" translatesAutoresizingMaskIntoConstraints="NO" id="2jg-Ct-0t0">
+                    <rect key="frame" x="20" y="49" width="225" height="215"/>
+                    <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
+                    <imageCell key="cell" refusesFirstResponder="YES" alignment="left" imageScaling="proportionallyDown" image="upload" id="SQf-YI-nXZ"/>
+                </imageView>
+                <customView fixedFrame="YES" translatesAutoresizingMaskIntoConstraints="NO" id="MI0-Tw-K0l" customClass="DropView" customModule="Screenshottr" customModuleProvider="target">
+                    <rect key="frame" x="20" y="49" width="225" height="215"/>
+                    <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
+                    <subviews>
+                        <textField horizontalHuggingPriority="251" verticalHuggingPriority="750" fixedFrame="YES" translatesAutoresizingMaskIntoConstraints="NO" id="fj4-kJ-fXa">
+                            <rect key="frame" x="-2" y="20" width="229" height="17"/>
+                            <autoresizingMask key="autoresizingMask"/>
+                            <textFieldCell key="cell" lineBreakMode="clipping" alignment="center" title="Drag and Drop to Upload" id="dcJ-qF-u2q">
+                                <font key="font" metaFont="system"/>
+                                <color key="textColor" name="labelColor" catalog="System" colorSpace="catalog"/>
+                                <color key="backgroundColor" name="textBackgroundColor" catalog="System" colorSpace="catalog"/>
+                            </textFieldCell>
+                        </textField>
+                    </subviews>
+                </customView>
                 <button verticalHuggingPriority="750" fixedFrame="YES" translatesAutoresizingMaskIntoConstraints="NO" id="ZlR-St-Ru0">
-                    <rect key="frame" x="237" y="20" width="21" height="21"/>
+                    <rect key="frame" x="224" y="20" width="21" height="21"/>
                     <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
                     <buttonCell key="cell" type="square" bezelStyle="shadowlessSquare" image="NSActionTemplate" imagePosition="only" alignment="center" refusesFirstResponder="YES" imageScaling="proportionallyDown" inset="2" id="uPe-bE-h5R">
                         <behavior key="behavior" pushIn="YES" lightByBackground="YES" lightByGray="YES"/>
@@ -42,23 +63,6 @@
                         <action selector="toggleGearMenu:" target="-2" id="FKD-T9-7Xw"/>
                     </connections>
                 </button>
-                <imageView horizontalHuggingPriority="251" verticalHuggingPriority="251" fixedFrame="YES" translatesAutoresizingMaskIntoConstraints="NO" id="687-0U-0uf" customClass="DropView" customModule="Screenshottr" customModuleProvider="target">
-                    <rect key="frame" x="20" y="49" width="225" height="215"/>
-                    <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
-                    <imageCell key="cell" refusesFirstResponder="YES" alignment="left" imageScaling="proportionallyDown" image="upload" id="DPA-2I-1fC"/>
-                    <connections>
-                        <outlet property="textLabel" destination="r6E-aY-KOH" id="nQx-7n-fKo"/>
-                    </connections>
-                </imageView>
-                <textField verticalHuggingPriority="750" horizontalCompressionResistancePriority="250" fixedFrame="YES" translatesAutoresizingMaskIntoConstraints="NO" id="r6E-aY-KOH">
-                    <rect key="frame" x="5" y="95" width="254" height="23"/>
-                    <autoresizingMask key="autoresizingMask"/>
-                    <textFieldCell key="cell" lineBreakMode="truncatingTail" selectable="YES" alignment="center" title="Drag and Drop to Upload" usesSingleLineMode="YES" id="IqH-JI-SBr">
-                        <font key="font" metaFont="system"/>
-                        <color key="textColor" name="labelColor" catalog="System" colorSpace="catalog"/>
-                        <color key="backgroundColor" name="textBackgroundColor" catalog="System" colorSpace="catalog"/>
-                    </textFieldCell>
-                </textField>
             </subviews>
             <point key="canvasLocation" x="-17.5" y="62"/>
         </customView>
diff --git a/Screenshottr/UploadManager.swift b/Screenshottr/UploadManager.swift
index 6a663215c5ba03093bfb38d97e3b530247c6357c..a9bad596ec7efe75ae0fd99971212b85e2f97c29 100644
--- a/Screenshottr/UploadManager.swift
+++ b/Screenshottr/UploadManager.swift
@@ -24,7 +24,7 @@ class UploadManager: NSObject {
                 defaults.set(true, forKey: uploadingKey)
                 // This could probably be done better
                 // oh well lol
-                // sleep(2)
+                sleep(2) //prevents race condiiton on legacy Mac OS
                 let fileManager = FileManager.default
                 do {
                     // Grab contents by predicate, convert to array, loop through array with paths