diff --git a/changelog_unreleased/typescript/19565.md b/changelog_unreleased/typescript/19565.md
new file mode 100644
index 000000000..94d717f15
--- /dev/null
+++ b/changelog_unreleased/typescript/19565.md
@@ -0,0 +1,15 @@
+#### Fix comments being dropped on shorthand `type` import/export specifiers (#19565 by @kirkwaiblinger)
+
+<!-- prettier-ignore -->
+```tsx
+// Input
+export { type /* comment */ T } from "foo";
+import { type /* comment */ T } from "foo";
+
+// Prettier stable
+Error: Comment "comment" was not printed. Please report this error!
+
+// Prettier main
+export { type /* comment */ T } from "foo";
+import { type /* comment */ T } from "foo";
+```
diff --git a/src/language-js/comments/can-attach-comment.js b/src/language-js/comments/can-attach-comment.js
index a2abbacac..28a38e688 100644
--- a/src/language-js/comments/can-attach-comment.js
+++ b/src/language-js/comments/can-attach-comment.js
@@ -51,11 +51,11 @@ const isChildWontPrint = (node, [parent]) =>
     parent.value !== parent.key) ||
   (parent?.type === "ImportSpecifier" &&
     isShorthandSpecifier(parent) &&
-    parent.imported === node &&
-    parent.imported !== parent.local) ||
+    parent.local === node &&
+    parent.local !== parent.imported) ||
   (parent?.type === "ExportSpecifier" &&
     isShorthandSpecifier(parent) &&
-    parent.local === node &&
+    parent.exported === node &&
     parent.local !== parent.exported);
 
 /**
diff --git a/tests/format/typescript/import-export/__snapshots__/format.test.js.snap b/tests/format/typescript/import-export/__snapshots__/format.test.js.snap
index 34935c13b..ef245142d 100644
--- a/tests/format/typescript/import-export/__snapshots__/format.test.js.snap
+++ b/tests/format/typescript/import-export/__snapshots__/format.test.js.snap
@@ -116,6 +116,16 @@ import type { foo as bar } from 'baz';
 import type * as foo from './bar';
 import type foo from 'bar';
 
+// https://github.com/prettier/prettier/issues/19564
+export { type /* comment */ T } from 'foo';
+import { type /* comment */ T } from 'foo';
+
+export { /* e1 */ type /* e2 */ T /* e3 */ } from 'foo';
+import { /* i1 */ type /* i2 */ T /* i3 */ } from 'foo';
+
+export { /* e1 */ type /* e2 */ T /* e3 */ as /* e4 */ U /* e5 */ } from 'foo';
+import { /* i1 */ type /* i2 */ T /* i3 */ as /* i4 */ U /* i5 */ } from 'foo';
+
 =====================================output=====================================
 export type { SomeThing };
 export type { A as B };
@@ -132,5 +142,15 @@ import type { foo as bar } from "baz";
 import type * as foo from "./bar";
 import type foo from "bar";
 
+// https://github.com/prettier/prettier/issues/19564
+export { type /* comment */ T } from "foo";
+import { type /* comment */ T } from "foo";
+
+export { /* e1 */ type /* e2 */ T /* e3 */ } from "foo";
+import { /* i1 */ type /* i2 */ T /* i3 */ } from "foo";
+
+export { /* e1 */ type /* e2 */ T /* e3 */ as /* e4 */ U /* e5 */ } from "foo";
+import { /* i1 */ type /* i2 */ T /* i3 */ as /* i4 */ U /* i5 */ } from "foo";
+
 ================================================================================
 `;
diff --git a/tests/format/typescript/import-export/type-modifier.ts b/tests/format/typescript/import-export/type-modifier.ts
index cb24bb22b..072105c55 100644
--- a/tests/format/typescript/import-export/type-modifier.ts
+++ b/tests/format/typescript/import-export/type-modifier.ts
@@ -12,3 +12,13 @@ import type { foo, bar } from 'baz';
 import type { foo as bar } from 'baz';
 import type * as foo from './bar';
 import type foo from 'bar';
+
+// https://github.com/prettier/prettier/issues/19564
+export { type /* comment */ T } from 'foo';
+import { type /* comment */ T } from 'foo';
+
+export { /* e1 */ type /* e2 */ T /* e3 */ } from 'foo';
+import { /* i1 */ type /* i2 */ T /* i3 */ } from 'foo';
+
+export { /* e1 */ type /* e2 */ T /* e3 */ as /* e4 */ U /* e5 */ } from 'foo';
+import { /* i1 */ type /* i2 */ T /* i3 */ as /* i4 */ U /* i5 */ } from 'foo';