diff --git a/ShareX.HelpersLib/Controls/BlackStyle/BlackStyleCheckBox.cs b/ShareX.HelpersLib/Controls/BlackStyle/BlackStyleCheckBox.cs
index 3362945e6..de2e1f858 100644
--- a/ShareX.HelpersLib/Controls/BlackStyle/BlackStyleCheckBox.cs
+++ b/ShareX.HelpersLib/Controls/BlackStyle/BlackStyleCheckBox.cs
@@ -78,7 +78,7 @@ public override string Text
 
         public int SpaceAfterCheckBox { get; set; }
 
-        private bool isChecked;
+        private bool isChecked, isHover;
         private string text;
 
         private LinearGradientBrush backgroundBrush, backgroundCheckedBrush, innerBorderBrush, innerBorderCheckedBrush;
@@ -135,28 +135,18 @@ protected override void OnPaint(PaintEventArgs pe)
             }
         }
 
-        private void DrawBackground(Graphics g)
+        protected override void OnMouseEnter(EventArgs e)
         {
-            if (Checked)
-            {
-                g.FillRectangle(backgroundCheckedBrush, new Rectangle(2, 2, checkBoxSize - 4, checkBoxSize - 4));
-                g.DrawRectangle(innerBorderCheckedPen, new Rectangle(1, 1, checkBoxSize - 3, checkBoxSize - 3));
-            }
-            else
-            {
-                g.FillRectangle(backgroundBrush, new Rectangle(2, 2, checkBoxSize - 4, checkBoxSize - 4));
-                g.DrawRectangle(innerBorderPen, new Rectangle(1, 1, checkBoxSize - 3, checkBoxSize - 3));
-            }
-
-            g.DrawRectangle(borderPen, new Rectangle(0, 0, checkBoxSize - 1, checkBoxSize - 1));
+            base.OnMouseEnter(e);
+            isHover = true;
+            Refresh();
         }
 
-        private void DrawText(Graphics g)
+        protected override void OnMouseLeave(EventArgs e)
         {
-            Rectangle rect = new Rectangle(checkBoxSize + SpaceAfterCheckBox, 0, ClientRectangle.Width - checkBoxSize + SpaceAfterCheckBox, ClientRectangle.Height);
-            TextFormatFlags tff = TextFormatFlags.Left | TextFormatFlags.Top;
-            TextRenderer.DrawText(g, Text, Font, new Rectangle(rect.X, rect.Y + 1, rect.Width, rect.Height + 1), Color.Black, tff);
-            TextRenderer.DrawText(g, Text, Font, rect, ForeColor, tff);
+            base.OnMouseLeave(e);
+            isHover = false;
+            Refresh();
         }
 
         protected override void OnClick(EventArgs e)
@@ -174,6 +164,38 @@ protected virtual void OnCheckedChanged(EventArgs e)
             }
         }
 
+        private void DrawBackground(Graphics g)
+        {
+            if (Checked)
+            {
+                g.FillRectangle(backgroundCheckedBrush, new Rectangle(2, 2, checkBoxSize - 4, checkBoxSize - 4));
+                g.DrawRectangle(innerBorderCheckedPen, new Rectangle(1, 1, checkBoxSize - 3, checkBoxSize - 3));
+            }
+            else
+            {
+                g.FillRectangle(backgroundBrush, new Rectangle(2, 2, checkBoxSize - 4, checkBoxSize - 4));
+
+                if (isHover)
+                {
+                    g.DrawRectangle(innerBorderCheckedPen, new Rectangle(1, 1, checkBoxSize - 3, checkBoxSize - 3));
+                }
+                else
+                {
+                    g.DrawRectangle(innerBorderPen, new Rectangle(1, 1, checkBoxSize - 3, checkBoxSize - 3));
+                }
+            }
+
+            g.DrawRectangle(borderPen, new Rectangle(0, 0, checkBoxSize - 1, checkBoxSize - 1));
+        }
+
+        private void DrawText(Graphics g)
+        {
+            Rectangle rect = new Rectangle(checkBoxSize + SpaceAfterCheckBox, 0, ClientRectangle.Width - checkBoxSize + SpaceAfterCheckBox, ClientRectangle.Height);
+            TextFormatFlags tff = TextFormatFlags.Left | TextFormatFlags.Top | TextFormatFlags.WordBreak;
+            TextRenderer.DrawText(g, Text, Font, new Rectangle(rect.X, rect.Y + 1, rect.Width, rect.Height + 1), Color.Black, tff);
+            TextRenderer.DrawText(g, Text, Font, rect, ForeColor, tff);
+        }
+
         protected override void Dispose(bool disposing)
         {
             if (backgroundBrush != null) backgroundBrush.Dispose();
diff --git a/ShareX.HelpersLib/UpdateChecker/UpdateMessageBox.Designer.cs b/ShareX.HelpersLib/UpdateChecker/UpdateMessageBox.Designer.cs
index aedacb1b7..f4220533b 100644
--- a/ShareX.HelpersLib/UpdateChecker/UpdateMessageBox.Designer.cs
+++ b/ShareX.HelpersLib/UpdateChecker/UpdateMessageBox.Designer.cs
@@ -58,6 +58,7 @@ private void InitializeComponent()
             // 
             // cbDontShow
             // 
+            this.cbDontShow.BackColor = System.Drawing.Color.Transparent;
             resources.ApplyResources(this.cbDontShow, "cbDontShow");
             this.cbDontShow.ForeColor = System.Drawing.Color.White;
             this.cbDontShow.Name = "cbDontShow";
@@ -69,10 +70,10 @@ private void InitializeComponent()
             resources.ApplyResources(this, "$this");
             this.AutoScaleMode = System.Windows.Forms.AutoScaleMode.Font;
             this.BackColor = System.Drawing.Color.FromArgb(((int)(((byte)(70)))), ((int)(((byte)(70)))), ((int)(((byte)(70)))));
-            this.Controls.Add(this.cbDontShow);
             this.Controls.Add(this.lblText);
             this.Controls.Add(this.btnNo);
             this.Controls.Add(this.btnYes);
+            this.Controls.Add(this.cbDontShow);
             this.FormBorderStyle = System.Windows.Forms.FormBorderStyle.FixedSingle;
             this.MaximizeBox = false;
             this.Name = "UpdateMessageBox";
diff --git a/ShareX.HelpersLib/UpdateChecker/UpdateMessageBox.resx b/ShareX.HelpersLib/UpdateChecker/UpdateMessageBox.resx
index 030c76acf..a9f67453f 100644
--- a/ShareX.HelpersLib/UpdateChecker/UpdateMessageBox.resx
+++ b/ShareX.HelpersLib/UpdateChecker/UpdateMessageBox.resx
@@ -145,13 +145,13 @@
     <value>$this</value>
   </data>
   <data name="&gt;&gt;lblText.ZOrder" xml:space="preserve">
-    <value>1</value>
+    <value>0</value>
   </data>
   <data name="btnNo.Font" type="System.Drawing.Font, System.Drawing">
     <value>Arial, 12pt</value>
   </data>
   <data name="btnNo.Location" type="System.Drawing.Point, System.Drawing">
-    <value>280, 112</value>
+    <value>280, 120</value>
   </data>
   <data name="btnNo.Size" type="System.Drawing.Size, System.Drawing">
     <value>104, 32</value>
@@ -172,13 +172,13 @@
     <value>$this</value>
   </data>
   <data name="&gt;&gt;btnNo.ZOrder" xml:space="preserve">
-    <value>2</value>
+    <value>1</value>
   </data>
   <data name="btnYes.Font" type="System.Drawing.Font, System.Drawing">
     <value>Arial, 12pt</value>
   </data>
   <data name="btnYes.Location" type="System.Drawing.Point, System.Drawing">
-    <value>168, 112</value>
+    <value>168, 120</value>
   </data>
   <data name="btnYes.Size" type="System.Drawing.Size, System.Drawing">
     <value>104, 32</value>
@@ -199,22 +199,22 @@
     <value>$this</value>
   </data>
   <data name="&gt;&gt;btnYes.ZOrder" xml:space="preserve">
-    <value>3</value>
+    <value>2</value>
   </data>
   <data name="cbDontShow.Font" type="System.Drawing.Font, System.Drawing">
     <value>Arial, 8pt</value>
   </data>
   <data name="cbDontShow.Location" type="System.Drawing.Point, System.Drawing">
-    <value>8, 88</value>
+    <value>16, 88</value>
   </data>
   <data name="cbDontShow.Size" type="System.Drawing.Size, System.Drawing">
-    <value>376, 16</value>
+    <value>368, 32</value>
   </data>
   <data name="cbDontShow.TabIndex" type="System.Int32, mscorlib">
     <value>3</value>
   </data>
   <data name="cbDontShow.Text" xml:space="preserve">
-    <value>Don't show until next startup</value>
+    <value>Do not prompt again until ShareX starts next time</value>
   </data>
   <data name="&gt;&gt;cbDontShow.Name" xml:space="preserve">
     <value>cbDontShow</value>
@@ -226,7 +226,7 @@
     <value>$this</value>
   </data>
   <data name="&gt;&gt;cbDontShow.ZOrder" xml:space="preserve">
-    <value>0</value>
+    <value>3</value>
   </data>
   <metadata name="$this.Localizable" type="System.Boolean, mscorlib, Version=4.0.0.0, Culture=neutral, PublicKeyToken=b77a5c561934e089">
     <value>True</value>
@@ -235,7 +235,10 @@
     <value>6, 13</value>
   </data>
   <data name="$this.ClientSize" type="System.Drawing.Size, System.Drawing">
-    <value>399, 155</value>
+    <value>399, 168</value>
+  </data>
+  <data name="$this.ImeMode" type="System.Windows.Forms.ImeMode, System.Windows.Forms">
+    <value>NoControl</value>
   </data>
   <data name="$this.StartPosition" type="System.Windows.Forms.FormStartPosition, System.Windows.Forms">
     <value>CenterScreen</value>