diff --git a/spec-compliance-tests/babel-tests/check-babel-tests.ts b/spec-compliance-tests/babel-tests/check-babel-tests.ts
index 01f78d14..6ecae671 100644
--- a/spec-compliance-tests/babel-tests/check-babel-tests.ts
+++ b/spec-compliance-tests/babel-tests/check-babel-tests.ts
@@ -67,7 +67,6 @@ flow/scope/declare-module
 flow/this-annotation/function-type
 flow/typecasts/yield
 jsx/basic/3
-typescript/cast/as
 typescript/export/as-namespace
 typescript/import/export-import
 typescript/import/export-import-require
@@ -76,7 +75,6 @@ typescript/import/export-import-type-require
 typescript/import/import-default-id-type
 typescript/import/type-asi
 typescript/import/type-equals-require
-typescript/type-arguments/instantiation-expression-binary-operator
 `
   .split("\n")
   .filter((s) => s);
diff --git a/src/parser/plugins/typescript.ts b/src/parser/plugins/typescript.ts
index 10950613..cf57085b 100644
--- a/src/parser/plugins/typescript.ts
+++ b/src/parser/plugins/typescript.ts
@@ -1242,6 +1242,9 @@ export function tsParseSubscript(
       // Tagged template with a type argument.
       parseTemplate();
     } else if (
+      // The remaining possible case is an instantiation expression, e.g.
+      // Array<number> . Check for a few cases that would disqualify it and
+      // cause us to bail out.
       // a<b>>c is not (a<b>)>c, but a<(b>>c)
       state.type === tt.greaterThan ||
       // a<b>c is (a<b)>c
diff --git a/src/parser/tokenizer/index.ts b/src/parser/tokenizer/index.ts
index 3349a601..b02acb3d 100644
--- a/src/parser/tokenizer/index.ts
+++ b/src/parser/tokenizer/index.ts
@@ -536,7 +536,7 @@ function readToken_gt(): void {
 
 /**
  * Called after `as` expressions in TS; we're switching from a type to a
- * non-type context, so a > token may actually be >=
+ * non-type context, so a > token may actually be >= .
  */
 export function rescan_gt(): void {
   if (state.type === tt.greaterThan) {
@@ -565,7 +565,12 @@ function readToken_question(): void {
   // '?'
   const nextChar = input.charCodeAt(state.pos + 1);
   const nextChar2 = input.charCodeAt(state.pos + 2);
-  if (nextChar === charCodes.questionMark && !state.isType) {
+  if (
+    nextChar === charCodes.questionMark &&
+    // In Flow (but not TypeScript), ??string is a valid type that should be
+    // tokenized as two individual ? tokens.
+    !(isFlowEnabled && state.isType)
+  ) {
     if (nextChar2 === charCodes.equalsTo) {
       // '??='
       finishOp(tt.assign, 3);
diff --git a/test/flow-test.ts b/test/flow-test.ts
index cdad9228..b919f2d8 100644
--- a/test/flow-test.ts
+++ b/test/flow-test.ts
@@ -688,4 +688,15 @@ describe("transform flow", () => {
     `,
     );
   });
+
+  it("handles two ? operators in a row", () => {
+    assertFlowResult(
+      `
+      type T = ??number;
+    `,
+      `"use strict";
+      
+    `,
+    );
+  });
 });
diff --git a/test/typescript-test.ts b/test/typescript-test.ts
index a657a9ad..b220202e 100644
--- a/test/typescript-test.ts
+++ b/test/typescript-test.ts
@@ -5,6 +5,7 @@ import {
   IMPORT_DEFAULT_PREFIX,
   IMPORT_WILDCARD_PREFIX,
   JSX_PREFIX,
+  NULLISH_COALESCE_PREFIX,
   OPTIONAL_CHAIN_PREFIX,
 } from "./prefixes";
 import {assertResult, devProps} from "./util";
@@ -2388,15 +2389,17 @@ describe("typescript transform", () => {
     );
   });
 
-  it("properly handles a >= symbol after an `as` cast", () => {
+  it("properly handles >= and ?? after `as`", () => {
     assertTypeScriptResult(
       `
       const x: string | number = 1;
       if (x as number >= 5) {}
+      if (y as unknown ?? false) {}
     `,
-      `"use strict";
+      `"use strict";${NULLISH_COALESCE_PREFIX}
       const x = 1;
       if (x  >= 5) {}
+      if (_nullishCoalesce(y , () => ( false))) {}
     `,
     );
   });
@@ -3214,6 +3217,18 @@ describe("typescript transform", () => {
     );
   });
 
+  it("allows instantiation expressions followed by ??", () => {
+    assertResult(
+      `
+      const foo = a<b> ?? c;
+    `,
+      `${NULLISH_COALESCE_PREFIX}
+      const foo = _nullishCoalesce(a, () => ( c));
+    `,
+      {transforms: ["typescript"]},
+    );
+  });
+
   it("allows extends constraints on infer type variables", () => {
     assertResult(
       `