diff --git a/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/actual.js b/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/actual.js
new file mode 100644
index 0000000000..f6ee2a1d9d
--- /dev/null
+++ b/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/actual.js
@@ -0,0 +1,6 @@
+(function () {
+  let q;
+  let w;
+  let e;
+  if (true) [q, w, e] = [1, 2, 3].map(()=>123);
+})();
diff --git a/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/expected.js b/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/expected.js
new file mode 100644
index 0000000000..d28969c2ed
--- /dev/null
+++ b/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/expected.js
@@ -0,0 +1,17 @@
+(function () {
+  var q = void 0;
+  var w = void 0;
+  var e = void 0;
+
+  if (true) {
+    var _map = [1, 2, 3].map(function () {
+      return 123;
+    });
+
+    var _map2 = babelHelpers.slicedToArray(_map, 3);
+
+    q = _map2[0];
+    w = _map2[1];
+    e = _map2[2];
+  }
+})();
diff --git a/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/options.json b/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/options.json
new file mode 100644
index 0000000000..2dacc028c5
--- /dev/null
+++ b/packages/babel-plugin-transform-es2015-destructuring/test/fixtures/destructuring/issue-5628/options.json
@@ -0,0 +1,3 @@
+{
+  "plugins": ["external-helpers", "transform-es2015-arrow-functions", "transform-es2015-destructuring", "transform-es2015-spread", "transform-es2015-parameters", "transform-es2015-block-scoping", "transform-object-rest-spread", "transform-regenerator"]
+}
diff --git a/packages/babel-traverse/src/path/modification.js b/packages/babel-traverse/src/path/modification.js
index 104ed99aa7..afd395383f 100644
--- a/packages/babel-traverse/src/path/modification.js
+++ b/packages/babel-traverse/src/path/modification.js
@@ -104,6 +104,10 @@ export function _containerInsertAfter(nodes) {
  */
 
 export function insertAfter(nodes) {
+  return this._insertAfter(nodes);
+}
+
+export function _insertAfter(nodes, shouldRequeue = false) {
   this._assertUnremoved();
 
   nodes = this._verifyNodeList(nodes);
@@ -112,7 +116,10 @@ export function insertAfter(nodes) {
     this.parentPath.isExpressionStatement() ||
     this.parentPath.isLabeledStatement()
   ) {
-    return this.parentPath.insertAfter(nodes);
+    // `replaceWithMultiple` requeues if there's a replacement for this.node,
+    // but not for an ancestor's. Set `shouldRequeue` to true so that any replacement
+    // for an ancestor node can be enqueued. Fix #5628 and #5023.
+    return this.parentPath._insertAfter(nodes, true);
   } else if (
     this.isNodeType("Expression") ||
     (this.parentPath.isForStatement() && this.key === "init")
@@ -136,6 +143,9 @@ export function insertAfter(nodes) {
       nodes.unshift(this.node);
     }
     this._replaceWith(t.blockStatement(nodes));
+    if (shouldRequeue) {
+      this.requeue();
+    }
   } else {
     throw new Error(
       "We don't know what to do with this node type. " +