diff --git a/CHANGELOG.md b/CHANGELOG.md
index 6368be1..a419cb4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -39,6 +39,7 @@ Additions
 Fixes
 - Fixed images not updating their hidden state properly when the displayed texture changes
 - Fixed AutoInline elements overflowing into their parent if it's taller
+- Fixed Paragraph and Checkbox not reacting to SquishingGroup sizing properly
 
 Improvements
 - Increased Element area calculation recursion limit to 64
diff --git a/MLEM.Ui/Elements/Checkbox.cs b/MLEM.Ui/Elements/Checkbox.cs
index 1925202..291f8e6 100644
--- a/MLEM.Ui/Elements/Checkbox.cs
+++ b/MLEM.Ui/Elements/Checkbox.cs
@@ -106,13 +106,12 @@ namespace MLEM.Ui.Elements {
         }
 
         /// <inheritdoc />
-        protected override Vector2 CalcActualSize(RectangleF parentArea) {
-            var size = base.CalcActualSize(parentArea);
+        public override void SetAreaAndUpdateChildren(RectangleF area) {
+            base.SetAreaAndUpdateChildren(area);
             if (this.Label != null) {
-                this.Label.Size = new Vector2((size.X - size.Y) / this.Scale - this.TextOffsetX, 1);
-                this.Label.PositionOffset = new Vector2(size.Y / this.Scale + this.TextOffsetX, 0);
+                this.Label.Size = new Vector2((area.Width - area.Height) / this.Scale - this.TextOffsetX, 1);
+                this.Label.PositionOffset = new Vector2(area.Height / this.Scale + this.TextOffsetX, 0);
             }
-            return size;
         }
 
         /// <inheritdoc />
diff --git a/MLEM.Ui/Elements/Paragraph.cs b/MLEM.Ui/Elements/Paragraph.cs
index d73228c..1bd9eb1 100644
--- a/MLEM.Ui/Elements/Paragraph.cs
+++ b/MLEM.Ui/Elements/Paragraph.cs
@@ -175,6 +175,13 @@ namespace MLEM.Ui.Elements {
             this.CanBeMoused = false;
         }
 
+        /// <inheritdoc />
+        public override void SetAreaAndUpdateChildren(RectangleF area) {
+            base.SetAreaAndUpdateChildren(area);
+            // in case an outside source sets our area, we still want to display our text correctly
+            this.AlignAndSplitIfNecessary(area.Size);
+        }
+
         /// <inheritdoc />
         protected override Vector2 CalcActualSize(RectangleF parentArea) {
             var size = base.CalcActualSize(parentArea);
@@ -182,6 +189,9 @@ namespace MLEM.Ui.Elements {
             this.TokenizeIfNecessary();
             this.AlignAndSplitIfNecessary(size);
             var textSize = this.tokenizedText.GetArea(Vector2.Zero, this.TextScale * this.TextScaleMultiplier * this.Scale).Size;
+            // if we auto-adjust our width, then we would also split the same way with our adjusted width, so cache that
+            if (this.AutoAdjustWidth)
+                this.lastAlignSplitWidth = textSize.X;
             return new Vector2(this.AutoAdjustWidth ? textSize.X + this.ScaledPadding.Width : size.X, textSize.Y + this.ScaledPadding.Height);
         }
 
@@ -255,7 +265,7 @@ namespace MLEM.Ui.Elements {
             var width = size.X - this.ScaledPadding.Width;
             var scale = this.TextScale * this.TextScaleMultiplier * this.Scale;
 
-            if (this.lastAlignSplitWidth == width && this.lastAlignSplitScale == scale)
+            if (this.lastAlignSplitWidth?.Equals(width, Element.Epsilon) == true && this.lastAlignSplitScale?.Equals(scale, Element.Epsilon) == true)
                 return;
             this.lastAlignSplitWidth = width;
             this.lastAlignSplitScale = scale;