diff --git a/src/HelperManager.ts b/src/HelperManager.ts
index bd6235eb..cbc8be96 100644
--- a/src/HelperManager.ts
+++ b/src/HelperManager.ts
@@ -77,6 +77,12 @@ const HELPERS = {
       return value;
     }
   `,
+  optionalChainDelete: `
+    function optionalChainDelete(ops) {
+      const result = OPTIONAL_CHAIN_NAME(ops);
+      return result == null ? true : result;
+    }
+  `,
 };
 
 export class HelperManager {
@@ -95,8 +101,15 @@ export class HelperManager {
 
   emitHelpers(): string {
     let resultCode = "";
-    for (const [baseName, helperCode] of Object.entries(HELPERS)) {
+    if (this.helperNames.optionalChainDelete) {
+      this.getHelperName("optionalChain");
+    }
+    for (const [baseName, helperCodeTemplate] of Object.entries(HELPERS)) {
       const helperName = this.helperNames[baseName];
+      let helperCode = helperCodeTemplate;
+      if (baseName === "optionalChainDelete") {
+        helperCode = helperCode.replace("OPTIONAL_CHAIN_NAME", this.helperNames.optionalChain!);
+      }
       if (helperName) {
         resultCode += " ";
         resultCode += helperCode
diff --git a/src/TokenProcessor.ts b/src/TokenProcessor.ts
index 552c8a6d..4fb4dc9e 100644
--- a/src/TokenProcessor.ts
+++ b/src/TokenProcessor.ts
@@ -213,7 +213,11 @@ export default class TokenProcessor {
       }
     }
     if (token.isOptionalChainStart) {
-      this.resultCode += this.helperManager.getHelperName("optionalChain");
+      if (this.tokenIndex > 0 && this.tokenAtRelativeIndex(-1).type === tt._delete) {
+        this.resultCode += this.helperManager.getHelperName("optionalChainDelete");
+      } else {
+        this.resultCode += this.helperManager.getHelperName("optionalChain");
+      }
       this.resultCode += "([";
     }
   }
diff --git a/src/transformers/OptionalChainingNullishTransformer.ts b/src/transformers/OptionalChainingNullishTransformer.ts
index 85e9b607..c4bd173c 100644
--- a/src/transformers/OptionalChainingNullishTransformer.ts
+++ b/src/transformers/OptionalChainingNullishTransformer.ts
@@ -22,24 +22,42 @@ export default class OptionalChainingNullishTransformer extends Transformer {
       this.tokens.replaceTokenTrimmingLeftWhitespace(", () =>");
       return true;
     }
+    if (this.tokens.matches1(tt._delete)) {
+      const nextToken = this.tokens.tokenAtRelativeIndex(1);
+      if (nextToken.isOptionalChainStart) {
+        this.tokens.removeInitialToken();
+        return true;
+      }
+    }
     const token = this.tokens.currentToken();
-    if (
-      token.subscriptStartIndex != null &&
-      this.tokens.tokens[token.subscriptStartIndex].isOptionalChainStart
-    ) {
+    const chainStart = token.subscriptStartIndex;
+    if (chainStart != null && this.tokens.tokens[chainStart].isOptionalChainStart) {
       const param = this.nameManager.claimFreeName("_");
+      let arrowStartSnippet;
+      if (
+        chainStart > 0 &&
+        this.tokens.matches1AtIndex(chainStart - 1, tt._delete) &&
+        this.isLastSubscriptInChain()
+      ) {
+        // Delete operations are special: we already removed the delete keyword, and to still
+        // perform a delete, we need to insert a delete in the very last part of the chain, which
+        // in correct code will always be a property access.
+        arrowStartSnippet = `${param} => delete ${param}`;
+      } else {
+        arrowStartSnippet = `${param} => ${param}`;
+      }
       if (this.tokens.matches2(tt.questionDot, tt.parenL)) {
-        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'optionalCall', ${param} => ${param}`);
+        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'optionalCall', ${arrowStartSnippet}`);
       } else if (this.tokens.matches2(tt.questionDot, tt.bracketL)) {
-        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'optionalAccess', ${param} => ${param}`);
+        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'optionalAccess', ${arrowStartSnippet}`);
       } else if (this.tokens.matches1(tt.questionDot)) {
-        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'optionalAccess', ${param} => ${param}.`);
+        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'optionalAccess', ${arrowStartSnippet}.`);
       } else if (this.tokens.matches1(tt.dot)) {
-        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'access', ${param} => ${param}.`);
+        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'access', ${arrowStartSnippet}.`);
       } else if (this.tokens.matches1(tt.bracketL)) {
-        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'access', ${param} => ${param}[`);
+        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'access', ${arrowStartSnippet}[`);
       } else if (this.tokens.matches1(tt.parenL)) {
-        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'call', ${param} => ${param}(`);
+        this.tokens.replaceTokenTrimmingLeftWhitespace(`, 'call', ${arrowStartSnippet}(`);
       } else {
         throw new Error("Unexpected subscript operator in optional chain.");
       }
@@ -47,4 +65,35 @@ export default class OptionalChainingNullishTransformer extends Transformer {
     }
     return false;
   }
+
+  /**
+   * Determine if the current token is the last of its chain, so that we know whether it's eligible
+   * to have a delete op inserted.
+   *
+   * We can do this by walking forward until we determine one way or another. Each
+   * isOptionalChainStart token must be paired with exactly one isOptionalChainEnd token after it in
+   * a nesting way, so we can track depth and walk to the end of the chain (the point where the
+   * depth goes negative) and see if any other subscript token is after us in the chain.
+   */
+  isLastSubscriptInChain(): boolean {
+    let depth = 0;
+    for (let i = this.tokens.currentIndex() + 1; ; i++) {
+      if (i >= this.tokens.tokens.length) {
+        throw new Error("Reached the end of the code while finding the end of the access chain.");
+      }
+      if (this.tokens.tokens[i].isOptionalChainStart) {
+        depth++;
+      } else if (this.tokens.tokens[i].isOptionalChainEnd) {
+        depth--;
+      }
+      if (depth < 0) {
+        return true;
+      }
+
+      // This subscript token is a later one in the same chain.
+      if (depth === 0 && this.tokens.tokens[i].subscriptStartIndex != null) {
+        return false;
+      }
+    }
+  }
 }
diff --git a/test/prefixes.ts b/test/prefixes.ts
index 8a557bac..3ec9a3f8 100644
--- a/test/prefixes.ts
+++ b/test/prefixes.ts
@@ -28,3 +28,5 @@ if (op === 'access' || op === 'optionalAccess') { lastAccessLHS = value; value =
 else if (op === 'call' || op === 'optionalCall') { \
 value = fn((...args) => value.call(lastAccessLHS, ...args)); lastAccessLHS = undefined; \
 } } return value; }`;
+export const OPTIONAL_CHAIN_DELETE_PREFIX = ` function _optionalChainDelete(ops) { \
+const result = _optionalChain(ops); return result == null ? true : result; }`;
diff --git a/test/sucrase-test.ts b/test/sucrase-test.ts
index 4c49c8a9..a2a5807c 100644
--- a/test/sucrase-test.ts
+++ b/test/sucrase-test.ts
@@ -2,6 +2,7 @@ import {
   ESMODULE_PREFIX,
   IMPORT_DEFAULT_PREFIX,
   NULLISH_COALESCE_PREFIX,
+  OPTIONAL_CHAIN_DELETE_PREFIX,
   OPTIONAL_CHAIN_PREFIX,
 } from "./prefixes";
 import {assertOutput, assertResult} from "./util";
@@ -913,7 +914,7 @@ describe("sucrase", () => {
     );
   });
 
-  it("handles nested optional chain operations", () => {
+  it("handles nested nullish coalescing operations", () => {
     assertOutput(
       `
       setOutput(undefined ?? 7 ?? null);
@@ -976,4 +977,52 @@ describe("sucrase", () => {
       {transforms: []},
     );
   });
+
+  it("transpiles optional chain deletion", () => {
+    assertResult(
+      `
+      delete a?.b.c;
+    `,
+      `${OPTIONAL_CHAIN_PREFIX}${OPTIONAL_CHAIN_DELETE_PREFIX}
+       _optionalChainDelete([a, 'optionalAccess', _ => _.b, 'access', _2 => delete _2.c]);
+    `,
+      {transforms: []},
+    );
+  });
+
+  it("correctly identifies last element of optional chain deletion", () => {
+    assertResult(
+      `
+      delete a?.b[c?.c];
+    `,
+      `${OPTIONAL_CHAIN_PREFIX}${OPTIONAL_CHAIN_DELETE_PREFIX}
+       _optionalChainDelete([a, 'optionalAccess', _ => _.b, 'access', _2 => delete _2[_optionalChain([c, 'optionalAccess', _3 => _3.c])]]);
+    `,
+      {transforms: []},
+    );
+  });
+
+  it("deletes the property correctly with optional chain deletion", () => {
+    assertOutput(
+      `
+      const o = {x: 1};
+      delete o?.x;
+      setOutput(o.hasOwnProperty('x'))
+    `,
+      false,
+      {transforms: []},
+    );
+  });
+
+  it("does not crash with optional chain deletion on null", () => {
+    assertOutput(
+      `
+      const o = null;
+      delete o?.x;
+      setOutput(o)
+    `,
+      null,
+      {transforms: []},
+    );
+  });
 });