diff --git a/src/language-js/needs-parens.js b/src/language-js/needs-parens.js
index b0e2c03d..53144ec5 100644
--- a/src/language-js/needs-parens.js
+++ b/src/language-js/needs-parens.js
@@ -4,6 +4,7 @@ const assert = require("assert");
 
 const util = require("../common/util");
 const comments = require("./comments");
+const { hasFlowShorthandAnnotationComment } = require("./utils");
 
 function hasClosureCompilerTypeCastComment(text, path, locStart, locEnd) {
   // https://github.com/google/closure-compiler/wiki/Annotating-Types#type-casts
@@ -74,6 +75,16 @@ function needsParens(path, options) {
     return true;
   }
 
+  if (
+    // Preserve parens if we have a Flow annotation comment, unless we're using the Flow
+    // parser. The Flow parser turns Flow comments into type annotation nodes in its
+    // AST, which we handle separately.
+    options.parser !== "flow" &&
+    hasFlowShorthandAnnotationComment(path.getValue())
+  ) {
+    return true;
+  }
+
   // Identifiers never need parentheses.
   if (node.type === "Identifier") {
     return false;
diff --git a/src/language-js/printer-estree.js b/src/language-js/printer-estree.js
index 2be791f3..5342e305 100644
--- a/src/language-js/printer-estree.js
+++ b/src/language-js/printer-estree.js
@@ -34,6 +34,7 @@ const insertPragma = require("./pragma").insertPragma;
 const handleComments = require("./comments");
 const pathNeedsParens = require("./needs-parens");
 const preprocess = require("./preprocess");
+const { hasFlowShorthandAnnotationComment } = require("./utils");
 
 const {
   builders: {
@@ -166,6 +167,14 @@ function genericPrint(path, options, printPath, args) {
   parts.push(linesWithoutParens);
 
   if (needsParens) {
+    const node = path.getValue();
+    if (hasFlowShorthandAnnotationComment(node)) {
+      parts.push(" /*");
+      parts.push(node.trailingComments[0].value.trimLeft());
+      parts.push("*/");
+      node.trailingComments[0].printed = true;
+    }
+
     parts.push(")");
   }
 
@@ -2836,14 +2845,36 @@ function printPathNoParens(path, options, print, args) {
 
       return group(concat(parts));
     }
-    case "TypeCastExpression":
+    case "TypeCastExpression": {
+      const value = path.getValue();
+      // Flow supports a comment syntax for specifying type annotations: https://flow.org/en/docs/types/comments/.
+      // Unfortunately, its parser doesn't differentiate between comment annotations and regular
+      // annotations when producing an AST. So to preserve parentheses around type casts that use
+      // the comment syntax, we need to hackily read the source itself to see if the code contains
+      // a type annotation comment.
+      //
+      // Note that we're able to use the normal whitespace regex here because the Flow parser has
+      // already deemed this AST node to be a type cast. Only the Babylon parser needs the
+      // non-line-break whitespace regex, which is why hasFlowShorthandAnnotationComment() is
+      // implemented differently.
+      const commentSyntax =
+        value &&
+        value.typeAnnotation &&
+        value.typeAnnotation.range &&
+        options.originalText
+          .substring(value.typeAnnotation.range[0])
+          .match(/^\/\*\s*:/);
       return concat([
         "(",
         path.call(print, "expression"),
+        commentSyntax ? " /*" : "",
         ": ",
         path.call(print, "typeAnnotation"),
+        commentSyntax ? " */" : "",
         ")"
       ]);
+    }
+
     case "TypeParameterDeclaration":
     case "TypeParameterInstantiation":
     case "TSTypeParameterDeclaration":
@@ -5994,7 +6025,7 @@ function willPrintOwnComments(path) {
   const parent = path.getParentNode();
 
   return (
-    ((node && isJSXNode(node)) ||
+    ((node && (isJSXNode(node) || hasFlowShorthandAnnotationComment(node))) ||
       (parent &&
         (parent.type === "JSXSpreadAttribute" ||
           parent.type === "JSXSpreadChild" ||
diff --git a/src/language-js/utils.js b/src/language-js/utils.js
new file mode 100644
index 00000000..11225546
--- /dev/null
+++ b/src/language-js/utils.js
@@ -0,0 +1,26 @@
+"use strict";
+
+function hasFlowShorthandAnnotationComment(node) {
+  // https://flow.org/en/docs/types/comments/
+  // Syntax example: const r = new (window.Request /*: Class<Request> */)("");
+
+  return (
+    node.extra &&
+    node.extra.parenthesized &&
+    node.trailingComments &&
+    // We match any whitespace except line terminators because
+    // Flow annotation comments cannot be split across lines. For example:
+    //
+    // (this /*
+    // : any */).foo = 5;
+    //
+    // is not picked up by Flow (see https://github.com/facebook/flow/issues/7050), so
+    // removing the newline would create a type annotation that the user did not intend
+    // to create.
+    node.trailingComments[0].value.match(/^(?:(?=.)\s)*:/)
+  );
+}
+
+module.exports = {
+  hasFlowShorthandAnnotationComment
+};
diff --git a/tests/flow_comments/__snapshots__/jsfmt.spec.js.snap b/tests/flow_comments/__snapshots__/jsfmt.spec.js.snap
index 8f45bdf4..6b3ebd34 100644
--- a/tests/flow_comments/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/flow_comments/__snapshots__/jsfmt.spec.js.snap
@@ -85,3 +85,32 @@ type Props = {
 };
 
 `;
+
+exports[`type_annotations.js - flow-verify 1`] = `
+new (window.Request/*: Class<Request> */)("");
+
+(this/*: any */).foo = 5;
+
+(this/*    : any */).foo = 5;
+
+// This next example illustrates that Prettier will not remove a line break
+// and unintentionally create a type annotation that was not there before.
+(this/*
+: any */).foo = 5;
+
+const x = (input /*: string */) /*: string */ => {};
+~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+new (window.Request /*: Class<Request> */)("");
+
+(this /*: any */).foo = 5;
+
+(this /*: any */).foo = 5;
+
+// This next example illustrates that Prettier will not remove a line break
+// and unintentionally create a type annotation that was not there before.
+this /*
+: any */.foo = 5;
+
+const x = (input /*: string */) /*: string */ => {};
+
+`;
diff --git a/tests/flow_comments/type_annotations.js b/tests/flow_comments/type_annotations.js
new file mode 100644
index 00000000..0cafa44e
--- /dev/null
+++ b/tests/flow_comments/type_annotations.js
@@ -0,0 +1,12 @@
+new (window.Request/*: Class<Request> */)("");
+
+(this/*: any */).foo = 5;
+
+(this/*    : any */).foo = 5;
+
+// This next example illustrates that Prettier will not remove a line break
+// and unintentionally create a type annotation that was not there before.
+(this/*
+: any */).foo = 5;
+
+const x = (input /*: string */) /*: string */ => {};