diff --git a/native/cpp/CommonCpp/CryptoTools/CryptoModule.cpp b/native/cpp/CommonCpp/CryptoTools/CryptoModule.cpp
index 2ed7bfa80d..7c9ba9b164 100644
--- a/native/cpp/CommonCpp/CryptoTools/CryptoModule.cpp
+++ b/native/cpp/CommonCpp/CryptoTools/CryptoModule.cpp
@@ -121,6 +121,24 @@ bool CryptoModule::prekeyExistsAndOlderThan(uint64_t threshold) {
   return currentTime - lastPrekeyPublishTime >= threshold;
 }
 
+bool CryptoModule::prekeyDoesntExist() {
+  // Prekey generation when creating an Olm Account was added to clients
+  // after the initial launch of Olm. Because of that, there is a high
+  // chance there are users who have the account without a generated prekey.
+
+  // When prekey or signature is empty it contains bytes with only 0 values.
+  // Because of Base64 encoding, 0 is encoded as char `A` and empty
+  // prekey/signature is a string built from only `A`'s.
+  const std::string emptyPrekey(KEYSIZE, 'A');
+  const std::string emptySignature(SIGNATURESIZE, 'A');
+
+  std::string prekey = this->getPrekey();
+  std::string signature = this->getPrekeySignature();
+
+  return prekey.find(emptyPrekey) != std::string::npos ||
+      signature == emptySignature;
+}
+
 Keys CryptoModule::keysFromStrings(
     const std::string &identityKeys,
     const std::string &oneTimeKeys) {
@@ -455,6 +473,11 @@ std::optional<std::string> CryptoModule::validatePrekey() {
   static const uint64_t maxOldPrekeyAge = 2 * 60;
   std::optional<std::string> maybeNewPrekey;
 
+  bool prekeyDoesntExist = this->prekeyDoesntExist();
+  if (prekeyDoesntExist) {
+    return this->generateAndGetPrekey();
+  }
+
   bool shouldRotatePrekey =
       this->prekeyExistsAndOlderThan(maxPrekeyPublishTime);
   if (shouldRotatePrekey) {
diff --git a/native/cpp/CommonCpp/CryptoTools/CryptoModule.h b/native/cpp/CommonCpp/CryptoTools/CryptoModule.h
index b6066afd4c..2b61f448c4 100644
--- a/native/cpp/CommonCpp/CryptoTools/CryptoModule.h
+++ b/native/cpp/CommonCpp/CryptoTools/CryptoModule.h
@@ -29,6 +29,7 @@ class CryptoModule {
   // returns number of published keys
   size_t publishOneTimeKeys();
   bool prekeyExistsAndOlderThan(uint64_t threshold);
+  bool prekeyDoesntExist();
   OlmBuffer pickleAccount(const std::string &secretKey);
 
 public: