diff --git a/packages/babel-generator/src/printer.ts b/packages/babel-generator/src/printer.ts
index 1a0c6e2a7af0..f55ec31cfb93 100644
--- a/packages/babel-generator/src/printer.ts
+++ b/packages/babel-generator/src/printer.ts
@@ -2,7 +2,7 @@ import Buffer from "./buffer";
 import type { Loc } from "./buffer";
 import * as n from "./node";
 import type * as t from "@babel/types";
-import { isProperty, isFunction, isStatement } from "@babel/types";
+import { isProperty, isFunction, isStatement, isLVal } from "@babel/types";
 import type {
   RecordAndTuplePluginOptions,
   PipelineOperatorPluginOptions,
@@ -1011,14 +1011,20 @@ class Printer {
         } else {
           hasLoc = false;
 
-          if (len === 1 && type === COMMENT_TYPE.LEADING) {
-            this._printComment(
-              comment,
-              (!isStatement(node) && !isProperty(node)) ||
-                isFunction(parent, { body: node })
-                ? COMMENT_SKIP_NEWLINE.SKIP_ALL
-                : COMMENT_SKIP_NEWLINE.DEFAULT,
-            );
+          if (len === 1) {
+            if (type === COMMENT_TYPE.LEADING) {
+              this._printComment(
+                comment,
+                (!isStatement(node) && !isProperty(node)) ||
+                  isFunction(parent, { body: node })
+                  ? COMMENT_SKIP_NEWLINE.SKIP_ALL
+                  : COMMENT_SKIP_NEWLINE.DEFAULT,
+              );
+            } else if (type === COMMENT_TYPE.TRAILING && isLVal(node)) {
+              this._printComment(comment, COMMENT_SKIP_NEWLINE.SKIP_ALL);
+            } else {
+              this._printComment(comment, COMMENT_SKIP_NEWLINE.DEFAULT);
+            }
           } else if (
             type === COMMENT_TYPE.INNER &&
             !(node.type === "ObjectExpression" && node.properties.length > 1) &&
diff --git a/packages/babel-plugin-transform-flow-comments/test/fixtures/flow-comments/class-prop-values/output.js b/packages/babel-plugin-transform-flow-comments/test/fixtures/flow-comments/class-prop-values/output.js
index a993e304e28e..bb9997322925 100644
--- a/packages/babel-plugin-transform-flow-comments/test/fixtures/flow-comments/class-prop-values/output.js
+++ b/packages/babel-plugin-transform-flow-comments/test/fixtures/flow-comments/class-prop-values/output.js
@@ -1,4 +1,5 @@
 class X {
   foo = 2;
-  bar /*: number*/ = 3; /*:: baz: ?string*/
+  bar /*: number*/ = 3;
+  /*:: baz: ?string*/
 }
diff --git a/packages/babel-plugin-transform-flow-comments/test/fixtures/flow-comments/type-cast/output.js b/packages/babel-plugin-transform-flow-comments/test/fixtures/flow-comments/type-cast/output.js
index 1b2c5f2b1fca..adfbff51872f 100644
--- a/packages/babel-plugin-transform-flow-comments/test/fixtures/flow-comments/type-cast/output.js
+++ b/packages/babel-plugin-transform-flow-comments/test/fixtures/flow-comments/type-cast/output.js
@@ -1,2 +1,4 @@
 var a = (y /*: any*/);
-var a = ((y /*: foo*/) /*: any*/);
+var a = ((y /*: foo*/)
+/*: any*/
+);