diff --git a/src/types.ts b/src/types.ts
index 08c4300..decd170 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -253,12 +253,17 @@ export function createOptionalCallbackFunction<T, A extends unknown[]>(
   return ((...args: A | [...A, ErrorFirstCallback<T>]) => {
     const possibleCallback = args[args.length - 1];
     if (isErrorFirstCallback(possibleCallback)) {
+      let result: T;
+      // Only `syncVersion` may run inside the `try`. Invoking the callback there would let an
+      // exception thrown *by the callback* land in the `catch` and invoke it a second time.
+      // https://github.com/node-saml/xml-crypto/issues/527
       try {
-        const result = syncVersion(...(args.slice(0, -1) as A));
-        possibleCallback(null, result);
+        result = syncVersion(...(args.slice(0, -1) as A));
       } catch (err) {
         possibleCallback(err instanceof Error ? err : new Error("Unknown error"));
+        return;
       }
+      possibleCallback(null, result);
     } else {
       return syncVersion(...(args as A));
     }
diff --git a/test/types-tests.spec.ts b/test/types-tests.spec.ts
new file mode 100644
index 0000000..348e7ad
--- /dev/null
+++ b/test/types-tests.spec.ts
@@ -0,0 +1,28 @@
+import { SignedXml, type ErrorFirstCallback } from "../src/index";
+import * as fs from "fs";
+import { expect } from "chai";
+
+describe("Callback invocation", function () {
+  // https://github.com/node-saml/xml-crypto/issues/527
+  it("invokes the callback once when the callback throws", function () {
+    const xml = `<x xmlns:wsu='http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-wssecurity-utility-1.0.xsd' Id='_1'></x>`;
+    const sig = new SignedXml();
+    sig.privateKey = fs.readFileSync("./test/static/client.pem");
+    sig.addReference({
+      xpath: "//*[local-name(.)='x']",
+      digestAlgorithm: "http://www.w3.org/2000/09/xmldsig#sha1",
+      transforms: ["http://www.w3.org/2001/10/xml-exc-c14n#"],
+    });
+    sig.canonicalizationAlgorithm = "http://www.w3.org/2001/10/xml-exc-c14n#";
+    sig.signatureAlgorithm = "http://www.w3.org/2000/09/xmldsig#rsa-sha1";
+
+    const errorsSeen: (string | null)[] = [];
+    const callback: ErrorFirstCallback<SignedXml> = (err) => {
+      errorsSeen.push(err ? err.message : null);
+      throw new Error("Error Thrown");
+    };
+
+    expect(() => sig.computeSignature(xml, callback)).to.throw("Error Thrown");
+    expect(errorsSeen).to.deep.equal([null]);
+  });
+});