diff --git a/src/main/kotlin/net/shadowfacts/cacao/view/Label.kt b/src/main/kotlin/net/shadowfacts/cacao/view/Label.kt
index a6e6bc0..02e9aef 100644
--- a/src/main/kotlin/net/shadowfacts/cacao/view/Label.kt
+++ b/src/main/kotlin/net/shadowfacts/cacao/view/Label.kt
@@ -80,11 +80,12 @@ class Label(
 		updateIntrinsicContentSize(false)
 	}
 
-	private fun updateIntrinsicContentSize(canWrap: Boolean): Boolean {
+	private fun updateIntrinsicContentSize(canWrap: Boolean, isFromDidLayout: Boolean = false): Boolean {
 		if (RenderHelper.disabled) return false
 
 		val oldSize = intrinsicContentSize
-		if (wrappingMode == WrappingMode.WRAP && canWrap && hasSolver) {
+		// don't wrap until we've laid out without wrapping to ensure the current bounds reflect the maximum available space
+		if (wrappingMode == WrappingMode.WRAP && canWrap && hasSolver && isFromDidLayout) {
 			val lines = textRenderer.wrapLines(text, bounds.width.toInt())
 			val height = (if (maxLines == 0) lines.size else min(lines.size, maxLines)) * textRenderer.fontHeight
 			intrinsicContentSize = Size(bounds.width, height.toDouble())
@@ -120,7 +121,7 @@ class Label(
 		super.didLayout()
 
 		computeLines()
-		if (updateIntrinsicContentSize(true)) {
+		if (updateIntrinsicContentSize(true, true)) {
 			// if the intrinsic content size changes, relayout
 			window!!.layout()
 		}