diff --git a/src/wp-admin/js/customize-controls.js b/src/wp-admin/js/customize-controls.js
index 5c0d0a40fa..5c21af6be4 100644
--- a/src/wp-admin/js/customize-controls.js
+++ b/src/wp-admin/js/customize-controls.js
@@ -2097,22 +2097,22 @@
 				xInit = parseInt( control.params.width, 10 ),
 				yInit = parseInt( control.params.height, 10 ),
 				ratio = xInit / yInit,
-				xImg  = realWidth,
-				yImg  = realHeight,
+				xImg  = xInit,
+				yImg  = yInit,
 				x1, y1, imgSelectOptions;
 
 			controller.set( 'canSkipCrop', ! control.mustBeCropped( flexWidth, flexHeight, xInit, yInit, realWidth, realHeight ) );
 
-			if ( xImg / yImg > ratio ) {
-				yInit = yImg;
+			if ( realWidth / realHeight > ratio ) {
+				yInit = realHeight;
 				xInit = yInit * ratio;
 			} else {
-				xInit = xImg;
+				xInit = realWidth;
 				yInit = xInit / ratio;
 			}
 
-			x1 = ( xImg - xInit ) / 2;
-			y1 = ( yImg - yInit ) / 2;
+			x1 = ( realWidth - xInit ) / 2;
+			y1 = ( realHeight - yInit ) / 2;
 
 			imgSelectOptions = {
 				handles: true,
@@ -2121,6 +2121,8 @@
 				persistent: true,
 				imageWidth: realWidth,
 				imageHeight: realHeight,
+				minWidth: xImg > xInit ? xInit : xImg,
+				minHeight: yImg > yInit ? yInit : yImg,
 				x1: x1,
 				y1: y1,
 				x2: xInit + x1,
@@ -2130,11 +2132,15 @@
 			if ( flexHeight === false && flexWidth === false ) {
 				imgSelectOptions.aspectRatio = xInit + ':' + yInit;
 			}
-			if ( flexHeight === false ) {
-				imgSelectOptions.maxHeight = yInit;
+
+			if ( true === flexHeight ) {
+				delete imgSelectOptions.minHeight;
+				imgSelectOptions.maxWidth = realWidth;
 			}
-			if ( flexWidth === false ) {
-				imgSelectOptions.maxWidth = xInit;
+
+			if ( true === flexWidth ) {
+				delete imgSelectOptions.minWidth;
+				imgSelectOptions.maxHeight = realHeight;
 			}
 
 			return imgSelectOptions;