diff --git a/src/printer.js b/src/printer.js
index dc4c9d95d..f3cef8d08 100644
--- a/src/printer.js
+++ b/src/printer.js
@@ -2270,12 +2270,9 @@ function isEmptyJSXElement(node) {
 //
 // For another, leading, trailing, and lone whitespace all need to
 // turn themselves into the rather ugly `{' '}` when breaking.
-function printJSXChildren(path, options, print) {
+function printJSXChildren(path, options, print, jsxWhitespace) {
   const n = path.getValue();
   const children = [];
-  const jsxWhitespace = options.singleQuote
-    ? ifBreak("{' '}", " ")
-    : ifBreak('{" "}', " ");
 
   // using `map` instead of `each` because it provides `i`
   path.map(
@@ -2385,7 +2382,10 @@ function printJSXElement(path, options, print) {
     return openingLines;
   }
 
-  const children = printJSXChildren(path, options, print);
+  const jsxWhitespace = options.singleQuote
+    ? ifBreak("{' '}", " ")
+    : ifBreak('{" "}', " ");
+  const children = printJSXChildren(path, options, print, jsxWhitespace);
   let forcedBreak = false;
 
   // Trim trailing lines, recording if there was a hardline
@@ -2417,46 +2417,47 @@ function printJSXElement(path, options, print) {
   }
 
   // Group by line, recording if there was a hardline.
-  let childrenGroupedByLine;
-  if (children.length === 1) {
-    if (!forcedBreak && willBreak(children[0])) {
-      forcedBreak = true;
+  let groups = [[]]; // Initialize the first line's group
+  children.forEach((child, i) => {
+    // leading and trailing JSX whitespace don't go into a group
+    if (child === jsxWhitespace) {
+      if (i === 0) {
+        groups.unshift(child);
+        return;
+      } else if (i === children.length - 1) {
+        groups.push(child);
+        return;
+      }
     }
 
-    // Don't wrap a single child in a group as there is no need, and a
-    // lone JSX whitespace doesn't work otherwise because the group
-    // will be printed in flat mode, and we need to print `{' '}` in
-    // break mode.
-    childrenGroupedByLine = [concat([hardline, children[0]])];
-  } else {
-    // Prefill leading newline, and initialize the first line's group
-    let groups = [[]];
-    children.forEach((child, i) => {
-      let prev = children[i - 1];
-      if (prev && willBreak(prev)) {
-        forcedBreak = true;
+    let prev = children[i - 1];
+    if (prev && willBreak(prev)) {
+      forcedBreak = true;
 
-        // On a new line, so create a new group and put this element
-        // in it.
-        groups.push([child]);
-      } else {
-        // Not on a newline, so add this element to the current group.
-        util.getLast(groups).push(child);
-      }
+      // On a new line, so create a new group and put this element in it.
+      groups.push([child]);
+    } else {
+      // Not on a newline, so add this element to the current group.
+      util.getLast(groups).push(child);
+    }
 
-      // Ensure we record hardline of last element.
-      if (!forcedBreak && i === children.length - 1) {
-        if (willBreak(child)) forcedBreak = true;
-      }
-    });
+    // Ensure we record hardline of last element.
+    if (!forcedBreak && i === children.length - 1) {
+      if (willBreak(child)) forcedBreak = true;
+    }
+  });
 
-    childrenGroupedByLine = [
-      hardline,
-      // Conditional groups suppress break propagation; we want output
-      // hard lines without breaking up the entire jsx element.
-      concat(groups.map(contents => conditionalGroup([concat(contents)])))
-    ];
-  }
+  const childrenGroupedByLine = [
+    hardline,
+    // Conditional groups suppress break propagation; we want to output
+    // hard lines without breaking up the entire jsx element.
+    // Note that leading and trailing JSX Whitespace don't go into a group.
+    concat(groups.map(contents =>
+      Array.isArray(contents)
+        ? conditionalGroup([concat(contents)])
+        : contents
+    ))
+  ];
 
   const closingLines = path.call(print, "closingElement");
 
diff --git a/tests/flow/more_react/__snapshots__/jsfmt.spec.js.snap b/tests/flow/more_react/__snapshots__/jsfmt.spec.js.snap
index 4bebcc2b9..3a2682fdc 100644
--- a/tests/flow/more_react/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/flow/more_react/__snapshots__/jsfmt.spec.js.snap
@@ -126,7 +126,7 @@ var App = require(\"App.react\");
 
 var app = (
   <App y={42}>
-     // error, y: number but foo expects string in App.react
+    {\" \"}// error, y: number but foo expects string in App.react
     Some text.
   </App>
 );
diff --git a/tests/jsx-significant-space/__snapshots__/jsfmt.spec.js.snap b/tests/jsx-significant-space/__snapshots__/jsfmt.spec.js.snap
index 177f1bf34..e48419f18 100644
--- a/tests/jsx-significant-space/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/jsx-significant-space/__snapshots__/jsfmt.spec.js.snap
@@ -48,6 +48,21 @@ nest_plz =
     <div></div>
     </div>
   </div>
+
+regression_not_transformed_1 =
+  <span> <Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" /></span>;
+
+regression_not_transformed_2 =
+  <span><Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" /> </span>;
+
+similar_1 =
+  <span> <Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" /></span>;
+
+similar_2 =
+  <span><Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" /> </span>;
+
+similar_3 =
+  <span><Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" /> <Icon icon=\"\" /></span>;
 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
 after = (
   <span>
@@ -113,5 +128,37 @@ nest_plz = (
     </div>
   </div>
 );
+
+regression_not_transformed_1 = (
+  <span>
+    {\" \"}<Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" />
+  </span>
+);
+
+regression_not_transformed_2 = (
+  <span>
+    <Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" />{\" \"}
+  </span>
+);
+
+similar_1 = (
+  <span>
+    {\" \"}
+    <Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" />
+  </span>
+);
+
+similar_2 = (
+  <span>
+    <Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" />
+    {\" \"}
+  </span>
+);
+
+similar_3 = (
+  <span>
+    <Icon icon=\"aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa\" /> <Icon icon=\"\" />
+  </span>
+);
 "
 `;
diff --git a/tests/jsx-significant-space/test.js b/tests/jsx-significant-space/test.js
index c39264395..31354e0c4 100644
--- a/tests/jsx-significant-space/test.js
+++ b/tests/jsx-significant-space/test.js
@@ -47,3 +47,18 @@ nest_plz =
     <div></div>
     </div>
   </div>
+
+regression_not_transformed_1 =
+  <span> <Icon icon="aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" /></span>;
+
+regression_not_transformed_2 =
+  <span><Icon icon="aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" /> </span>;
+
+similar_1 =
+  <span> <Icon icon="aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" /></span>;
+
+similar_2 =
+  <span><Icon icon="aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" /> </span>;
+
+similar_3 =
+  <span><Icon icon="aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" /> <Icon icon="" /></span>;