diff --git a/interface/src/commerce/Ledger.cpp b/interface/src/commerce/Ledger.cpp
index b0d293584c..33c23ccf2f 100644
--- a/interface/src/commerce/Ledger.cpp
+++ b/interface/src/commerce/Ledger.cpp
@@ -61,7 +61,7 @@ void Ledger::send(const QString& endpoint, const QString& success, const QString
 
 void Ledger::signedSend(const QString& propertyName, const QByteArray& text, const QString& key, const QString& endpoint, const QString& success, const QString& fail, const bool controlled_failure) {
     auto wallet = DependencyManager::get<Wallet>();
-    QString signature = key.isEmpty() ? "" : wallet->signWithKey(text, key);
+    QString signature = wallet->signWithKey(text, key); 
     QJsonObject request;
     request[propertyName] = QString(text);
     if (!controlled_failure) {
diff --git a/interface/src/commerce/Wallet.cpp b/interface/src/commerce/Wallet.cpp
index 69914e97a4..2f8a470b51 100644
--- a/interface/src/commerce/Wallet.cpp
+++ b/interface/src/commerce/Wallet.cpp
@@ -547,13 +547,16 @@ QStringList Wallet::listPublicKeys() {
 // the horror of code pages and so on (changing the bytes) by just returning a base64
 // encoded string representing the signature (suitable for http, etc...)
 QString Wallet::signWithKey(const QByteArray& text, const QString& key) {
-    qCInfo(commerce) << "Signing text" << text << "with key" << key;
     EC_KEY* ecPrivateKey = NULL;
+
+    auto keyFilePathString = keyFilePath().toStdString();
     if ((ecPrivateKey = readPrivateKey(keyFilePath().toStdString().c_str()))) {
         unsigned char* sig = new unsigned char[ECDSA_size(ecPrivateKey)];
 
         unsigned int signatureBytes = 0;
 
+        qCInfo(commerce) << "Signing text" << text << "with key at" << ecPrivateKey;
+
         QByteArray hashedPlaintext = QCryptographicHash::hash(text, QCryptographicHash::Sha256);
 
 
@@ -746,12 +749,10 @@ void Wallet::handleChallengeOwnershipPacket(QSharedPointer<ReceivedMessage> pack
     }
 
     EC_KEY_free(ec);
-    QByteArray ba = sig.toLocal8Bit();
-    const char *sigChar = ba.data();
 
     QByteArray textByteArray;
     if (status > -1) {
-        textByteArray = QByteArray(sigChar, (int) strlen(sigChar));
+        textByteArray = sig.toUtf8();
     }
     textByteArraySize = textByteArray.size();
     int certIDSize = certID.size();
diff --git a/libraries/entities/src/EntityItemProperties.cpp b/libraries/entities/src/EntityItemProperties.cpp
index 6e7fe9c1b2..9982f4d6a1 100644
--- a/libraries/entities/src/EntityItemProperties.cpp
+++ b/libraries/entities/src/EntityItemProperties.cpp
@@ -2540,11 +2540,15 @@ bool EntityItemProperties::verifySignature(const QString& publicKey, const QByte
                 ec);
             long error = ERR_get_error();
             if (error != 0 || answer == -1) {
-                const char* error_str = ERR_error_string(error, NULL);
-                qCWarning(entities) << "ERROR while verifying signature! EC error:" << error_str
+                qCWarning(entities) << "ERROR while verifying signature!"
                     << "\nKey:" << publicKey << "\nutf8 Key Length:" << keyLength
                     << "\nDigest:" << digest << "\nDigest Length:" << digestLength
                     << "\nSignature:" << signature << "\nSignature Length:" << signatureLength;
+                while (error != 0) {
+                    const char* error_str = ERR_error_string(error, NULL);
+                    qCWarning(entities) << "EC error:" << error_str;
+                    error = ERR_get_error();
+                }
             }
             EC_KEY_free(ec);
             if (bio) {
diff --git a/libraries/entities/src/EntityTree.cpp b/libraries/entities/src/EntityTree.cpp
index e62399ce95..3d5bf1dd12 100644
--- a/libraries/entities/src/EntityTree.cpp
+++ b/libraries/entities/src/EntityTree.cpp
@@ -1189,13 +1189,14 @@ bool EntityTree::verifyNonce(const QString& certID, const QString& nonce, Entity
         key = sent.second;
     }
 
-    QString annotatedKey = "-----BEGIN PUBLIC KEY-----\n" + key.insert(64, "\n") + "\n-----END PUBLIC KEY-----";
-    bool verificationSuccess = EntityItemProperties::verifySignature(annotatedKey.toUtf8(), actualNonce.toUtf8(), nonce.toUtf8());
+    QString annotatedKey = "-----BEGIN PUBLIC KEY-----\n" + key.insert(64, "\n") + "\n-----END PUBLIC KEY-----\n"; 
+    QByteArray hashedActualNonce = QCryptographicHash::hash(QByteArray::fromBase64(actualNonce.toUtf8()), QCryptographicHash::Sha256);
+    bool verificationSuccess = EntityItemProperties::verifySignature(annotatedKey.toUtf8(), hashedActualNonce, QByteArray::fromBase64(nonce.toUtf8()));
 
     if (verificationSuccess) {
         qCDebug(entities) << "Ownership challenge for Cert ID" << certID << "succeeded.";
     } else {
-        qCDebug(entities) << "Ownership challenge for Cert ID" << certID << "failed for nonce" << actualNonce << "key" << key << "signature" << nonce;
+        qCDebug(entities) << "Ownership challenge for Cert ID" << certID << "failed.\nHashed actual nonce (digest):" << hashedActualNonce << "\nSent nonce (signature)" << nonce << "\nKey" << key;
     }
 
     return verificationSuccess;