diff --git a/src/server/CMakeLists.txt b/src/server/CMakeLists.txt
index 00e348309..61545ccda 100644
--- a/src/server/CMakeLists.txt
+++ b/src/server/CMakeLists.txt
@@ -1,4 +1,4 @@
-add_executable(dragonfly dfly_main.cc)
+add_executable(dragonfly dfly_main.cc version_monitor.cc)
 cxx_link(dragonfly base dragonfly_lib)
 
 if (CMAKE_SYSTEM_PROCESSOR STREQUAL "x86_64" AND CMAKE_BUILD_TYPE STREQUAL "Release")
diff --git a/src/server/dfly_main.cc b/src/server/dfly_main.cc
index f51b8ae34..540038f4f 100644
--- a/src/server/dfly_main.cc
+++ b/src/server/dfly_main.cc
@@ -23,12 +23,10 @@
 #endif
 
 #include <mimalloc.h>
-#include <openssl/err.h>
 #include <signal.h>
 
 #include <iostream>
 #include <memory>
-#include <regex>
 
 #include "base/init.h"
 #include "base/proc_util.h"  // for GetKernelVersion
@@ -40,10 +38,10 @@
 #include "server/generic_family.h"
 #include "server/main_service.h"
 #include "server/version.h"
+#include "server/version_monitor.h"
 #include "strings/human_readable.h"
 #include "util/accept_server.h"
 #include "util/fibers/pool.h"
-#include "util/http/http_client.h"
 #include "util/varz.h"
 
 #ifdef __APPLE__
@@ -88,189 +86,6 @@ namespace {
 
 using util::http::TlsClient;
 
-std::optional<std::string> GetVersionString(const std::string& version_str) {
-  // The server sends a message such as {"latest": "0.12.0"}
-  const auto reg_match_expr = R"(\{\"latest"\:[ \t]*\"([0-9]+\.[0-9]+\.[0-9]+)\"\})";
-  VLOG(1) << "checking version '" << version_str << "'";
-  auto const regex = std::regex(reg_match_expr);
-  std::smatch match;
-  if (std::regex_match(version_str, match, regex) && match.size() > 1) {
-    // the second entry is the match to the group that holds the version string
-    return match[1].str();
-  } else {
-    LOG_FIRST_N(WARNING, 1) << "Remote version - invalid version number: '" << version_str << "'";
-    return std::nullopt;
-  }
-}
-
-std::optional<std::string> GetRemoteVersion(ProactorBase* proactor, SSL_CTX* ssl_context,
-                                            const std::string host, std::string_view service,
-                                            const std::string& resource,
-                                            const std::string& ver_header) {
-  namespace bh = boost::beast::http;
-  using ResponseType = bh::response<bh::string_body>;
-
-  bh::request<bh::string_body> req{bh::verb::get, resource, 11 /*http 1.1*/};
-  req.set(bh::field::host, host);
-  req.set(bh::field::user_agent, ver_header);
-  ResponseType res;
-  TlsClient http_client{proactor};
-  http_client.set_connect_timeout_ms(2000);
-
-  auto ec = http_client.Connect(host, service, ssl_context);
-
-  if (ec) {
-    LOG_FIRST_N(WARNING, 1) << "Remote version - connection error [" << host << ":" << service
-                            << "] : " << ec.message();
-    return nullopt;
-  }
-
-  ec = http_client.Send(req, &res);
-  if (!ec) {
-    VLOG(1) << "successfully got response from HTTP GET for host " << host << ":" << service << "/"
-            << resource << " response code is " << res.result();
-
-    if (res.result() == bh::status::ok) {
-      return GetVersionString(res.body());
-    }
-  } else {
-    static bool is_logged{false};
-    if (!is_logged) {
-      is_logged = true;
-
-#if (OPENSSL_VERSION_NUMBER >= 0x30000000L)
-      const char* func_err = "ssl_internal_error";
-#else
-      const char* func_err = ERR_func_error_string(ec.value());
-#endif
-
-      // Unfortunately AsioStreamAdapter looses the original error category
-      // because std::error_code can not be converted into boost::system::error_code.
-      // It's fixed in later versions of Boost, but for now we assume it's from TLS.
-      LOG(WARNING) << "Remote version - HTTP GET error [" << host << ":" << service << resource
-                   << "], error: " << ec.value();
-      LOG(WARNING) << "ssl error: " << func_err << "/" << ERR_reason_error_string(ec.value());
-    }
-  }
-
-  return nullopt;
-}
-
-struct VersionMonitor {
-  Fiber version_fiber_;
-  Done monitor_ver_done_;
-
-  void Run(ProactorPool* proactor_pool);
-
-  void Shutdown() {
-    monitor_ver_done_.Notify();
-    if (version_fiber_.IsJoinable()) {
-      version_fiber_.Join();
-    }
-  }
-
- private:
-  struct SslDeleter {
-    void operator()(SSL_CTX* ssl) {
-      if (ssl) {
-        TlsClient::FreeContext(ssl);
-      }
-    }
-  };
-
-  using SslPtr = std::unique_ptr<SSL_CTX, SslDeleter>;
-  void RunTask(SslPtr);
-
-  bool IsVersionOutdated(std::string_view remote, std::string_view current) const;
-};
-
-bool VersionMonitor::IsVersionOutdated(const std::string_view remote,
-                                       const std::string_view current) const {
-  const absl::InlinedVector<absl::string_view, 3> remote_xyz = absl::StrSplit(remote, ".");
-  const absl::InlinedVector<absl::string_view, 3> current_xyz = absl::StrSplit(current, ".");
-  if (remote_xyz.size() != current_xyz.size()) {
-    LOG(WARNING) << "Can't compare Dragonfly version " << current << " to latest version "
-                 << remote;
-    return false;
-  }
-  const auto print_to_log = [](const std::string_view version, const absl::string_view part) {
-    LOG(WARNING) << "Can't parse " << version << " part of version " << part << " as a number";
-  };
-  for (size_t i = 0; i < remote_xyz.size(); ++i) {
-    size_t remote_x = 0;
-    if (!absl::SimpleAtoi(remote_xyz[i], &remote_x)) {
-      print_to_log(remote, remote_xyz[i]);
-      return false;
-    }
-    size_t current_x = 0;
-    if (!absl::SimpleAtoi(current_xyz[i], &current_x)) {
-      print_to_log(current, current_xyz[i]);
-      return false;
-    }
-    if (remote_x > current_x) {
-      return true;
-    }
-
-    if (remote_x < current_x) {
-      return false;
-    }
-  }
-
-  return false;
-}
-
-void VersionMonitor::Run(ProactorPool* proactor_pool) {
-  // Avoid running dev environments.
-  if (getenv("DFLY_DEV_ENV")) {
-    LOG(WARNING) << "Running in dev environment (DFLY_DEV_ENV is set) - version monitoring is "
-                    "disabled";
-    return;
-  }
-  // not a production release tag.
-  if (!GetFlag(FLAGS_version_check) || kGitTag[0] != 'v' || strchr(kGitTag, '-')) {
-    return;
-  }
-
-  SslPtr ssl_ctx(TlsClient::CreateSslContext());
-  if (!ssl_ctx) {
-    VLOG(1) << "Remote version - failed to create SSL context - cannot run version monitoring";
-    return;
-  }
-
-  version_fiber_ = proactor_pool->GetNextProactor()->LaunchFiber(
-      [ssl_ctx = std::move(ssl_ctx), this]() mutable { RunTask(std::move(ssl_ctx)); });
-}
-
-void VersionMonitor::RunTask(SslPtr ssl_ctx) {
-  const auto loop_sleep_time = std::chrono::hours(24);  // every 24 hours
-
-  const std::string host_name = "version.dragonflydb.io";
-  const std::string_view port = "443";
-  const std::string resource = "/v1";
-  string_view current_version(kGitTag);
-
-  current_version.remove_prefix(1);
-  const std::string version_header = absl::StrCat("DragonflyDB/", current_version);
-
-  ProactorBase* my_pb = ProactorBase::me();
-  while (true) {
-    const std::optional<std::string> remote_version =
-        GetRemoteVersion(my_pb, ssl_ctx.get(), host_name, port, resource, version_header);
-    if (remote_version) {
-      const std::string_view rv = remote_version.value();
-      if (IsVersionOutdated(rv, current_version)) {
-        LOG_FIRST_N(INFO, 1) << "Your current version '" << current_version
-                             << "' is not the latest version. A newer version '" << rv
-                             << "' is now available. Please consider an update.";
-      }
-    }
-    if (monitor_ver_done_.WaitFor(loop_sleep_time)) {
-      VLOG(1) << "finish running version monitor task";
-      return;
-    }
-  }
-}
-
 enum class TermColor { kDefault, kRed, kGreen, kYellow };
 // Returns the ANSI color code for the given color. TermColor::kDefault is
 // an invalid input.
@@ -459,7 +274,11 @@ bool RunEngine(ProactorPool* pool, AcceptServer* acceptor) {
   service.Init(acceptor, listeners, opts);
 
   VersionMonitor version_monitor;
-  version_monitor.Run(pool);
+
+  // check if it's a production release tag.
+  if (GetFlag(FLAGS_version_check) && kGitTag[0] == 'v' && strchr(kGitTag, '-') == nullptr) {
+    version_monitor.Run(pool);
+  }
 
   // Start the acceptor loop and wait for the server to shutdown.
   acceptor->Run();
@@ -733,9 +552,9 @@ void PrintBasicUsageInfo() {
 
 void ParseFlagsFromEnv() {
   if (getenv("DFLY_PASSWORD")) {
-    LOG(WARNING)
-        << "DFLY_PASSWORD environment variable is being deprecated in favour of DFLY_requirepass";
+    LOG(FATAL) << "DFLY_PASSWORD environment variable was deprecated in favor of DFLY_requirepass";
   }
+
   // Allowed environment variable names that can have
   // DFLY_ prefix, but don't necessarily have an ABSL flag created
   absl::flat_hash_set<std::string_view> ignored_environment_flag_names = {"DEV_ENV", "PASSWORD"};
diff --git a/src/server/version_monitor.cc b/src/server/version_monitor.cc
new file mode 100644
index 000000000..aac827942
--- /dev/null
+++ b/src/server/version_monitor.cc
@@ -0,0 +1,184 @@
+// Copyright 2023, Roman Gershman.  All rights reserved.
+// See LICENSE for licensing terms.
+//
+
+#include "server/version_monitor.h"
+
+#include <absl/strings/str_split.h>
+#include <openssl/err.h>
+
+#include <boost/beast/http/string_body.hpp>
+#include <regex>
+
+#include "base/logging.h"
+#include "server/version.h"
+
+namespace dfly {
+
+using namespace std;
+using namespace util;
+using http::TlsClient;
+
+namespace {
+
+std::optional<std::string> GetVersionString(const std::string& version_str) {
+  // The server sends a message such as {"latest": "0.12.0"}
+  const auto reg_match_expr = R"(\{\"latest"\:[ \t]*\"([0-9]+\.[0-9]+\.[0-9]+)\"\})";
+  VLOG(1) << "checking version '" << version_str << "'";
+  auto const regex = std::regex(reg_match_expr);
+  std::smatch match;
+  if (std::regex_match(version_str, match, regex) && match.size() > 1) {
+    // the second entry is the match to the group that holds the version string
+    return match[1].str();
+  } else {
+    LOG_FIRST_N(WARNING, 1) << "Remote version - invalid version number: '" << version_str << "'";
+    return std::nullopt;
+  }
+}
+
+std::optional<std::string> GetRemoteVersion(ProactorBase* proactor, SSL_CTX* ssl_context,
+                                            const std::string host, std::string_view service,
+                                            const std::string& resource,
+                                            const std::string& ver_header) {
+  namespace bh = boost::beast::http;
+  using ResponseType = bh::response<bh::string_body>;
+
+  bh::request<bh::string_body> req{bh::verb::get, resource, 11 /*http 1.1*/};
+  req.set(bh::field::host, host);
+  req.set(bh::field::user_agent, ver_header);
+  ResponseType res;
+  TlsClient http_client{proactor};
+  http_client.set_connect_timeout_ms(2000);
+
+  auto ec = http_client.Connect(host, service, ssl_context);
+
+  if (ec) {
+    LOG_FIRST_N(WARNING, 1) << "Remote version - connection error [" << host << ":" << service
+                            << "] : " << ec.message();
+    return nullopt;
+  }
+
+  ec = http_client.Send(req, &res);
+  if (!ec) {
+    VLOG(1) << "successfully got response from HTTP GET for host " << host << ":" << service << "/"
+            << resource << " response code is " << res.result();
+
+    if (res.result() == bh::status::ok) {
+      return GetVersionString(res.body());
+    }
+  } else {
+    static bool is_logged{false};
+    if (!is_logged) {
+      is_logged = true;
+
+#if (OPENSSL_VERSION_NUMBER >= 0x30000000L)
+      const char* func_err = "ssl_internal_error";
+#else
+      const char* func_err = ERR_func_error_string(ec.value());
+#endif
+
+      // Unfortunately AsioStreamAdapter looses the original error category
+      // because std::error_code can not be converted into boost::system::error_code.
+      // It's fixed in later versions of Boost, but for now we assume it's from TLS.
+      LOG(WARNING) << "Remote version - HTTP GET error [" << host << ":" << service << resource
+                   << "], error: " << ec.value();
+      LOG(WARNING) << "ssl error: " << func_err << "/" << ERR_reason_error_string(ec.value());
+    }
+  }
+
+  return nullopt;
+}
+
+}  // namespace
+
+bool VersionMonitor::IsVersionOutdated(const std::string_view remote,
+                                       const std::string_view current) const {
+  const absl::InlinedVector<absl::string_view, 3> remote_xyz = absl::StrSplit(remote, ".");
+  const absl::InlinedVector<absl::string_view, 3> current_xyz = absl::StrSplit(current, ".");
+  if (remote_xyz.size() != current_xyz.size()) {
+    LOG(WARNING) << "Can't compare Dragonfly version " << current << " to latest version "
+                 << remote;
+    return false;
+  }
+  const auto print_to_log = [](const std::string_view version, const absl::string_view part) {
+    LOG(WARNING) << "Can't parse " << version << " part of version " << part << " as a number";
+  };
+  for (size_t i = 0; i < remote_xyz.size(); ++i) {
+    size_t remote_x = 0;
+    if (!absl::SimpleAtoi(remote_xyz[i], &remote_x)) {
+      print_to_log(remote, remote_xyz[i]);
+      return false;
+    }
+    size_t current_x = 0;
+    if (!absl::SimpleAtoi(current_xyz[i], &current_x)) {
+      print_to_log(current, current_xyz[i]);
+      return false;
+    }
+    if (remote_x > current_x) {
+      return true;
+    }
+
+    if (remote_x < current_x) {
+      return false;
+    }
+  }
+
+  return false;
+}
+
+void VersionMonitor::Run(ProactorPool* proactor_pool) {
+  // Avoid running dev environments.
+  if (getenv("DFLY_DEV_ENV")) {
+    LOG(WARNING) << "Running in dev environment (DFLY_DEV_ENV is set) - version monitoring is "
+                    "disabled";
+    return;
+  }
+
+  SslPtr ssl_ctx(TlsClient::CreateSslContext());
+  if (!ssl_ctx) {
+    VLOG(1) << "Remote version - failed to create SSL context - cannot run version monitoring";
+    return;
+  }
+
+  version_fiber_ = proactor_pool->GetNextProactor()->LaunchFiber(
+      [ssl_ctx = std::move(ssl_ctx), this]() mutable { RunTask(std::move(ssl_ctx)); });
+}
+
+void VersionMonitor::Shutdown() {
+  monitor_ver_done_.Notify();
+  if (version_fiber_.IsJoinable()) {
+    version_fiber_.Join();
+  }
+}
+
+void VersionMonitor::RunTask(SslPtr ssl_ctx) {
+  const auto loop_sleep_time = std::chrono::hours(24);  // every 24 hours
+
+  const std::string host_name = "version.dragonflydb.io";
+  const std::string_view port = "443";
+  const std::string resource = "/v1";
+  string_view current_version(kGitTag);
+
+  current_version.remove_prefix(1);
+  const std::string version_header = absl::StrCat("DragonflyDB/", current_version);
+
+  ProactorBase* my_pb = ProactorBase::me();
+  while (true) {
+    const std::optional<std::string> remote_version =
+        GetRemoteVersion(my_pb, ssl_ctx.get(), host_name, port, resource, version_header);
+    if (remote_version) {
+      const std::string_view rv = remote_version.value();
+      if (IsVersionOutdated(rv, current_version)) {
+        LOG_FIRST_N(INFO, 1) << "Your current version '" << current_version
+                             << "' is not the latest version. A newer version '" << rv
+                             << "' is now available. Please consider an update.";
+      }
+    }
+    if (monitor_ver_done_.WaitFor(loop_sleep_time)) {
+      VLOG(1) << "finish running version monitor task";
+      return;
+    }
+  }
+}
+
+}  // namespace dfly
diff --git a/src/server/version_monitor.h b/src/server/version_monitor.h
new file mode 100644
index 000000000..f3638cea0
--- /dev/null
+++ b/src/server/version_monitor.h
@@ -0,0 +1,36 @@
+// Copyright 2023, Roman Gershman.  All rights reserved.
+// See LICENSE for licensing terms.
+//
+#pragma once
+
+#include "util/fibers/fibers.h"
+#include "util/fibers/pool.h"
+#include "util/http/http_client.h"
+
+namespace dfly {
+
+class VersionMonitor {
+ public:
+  void Run(util::ProactorPool* proactor_pool);
+
+  void Shutdown();
+
+ private:
+  struct SslDeleter {
+    void operator()(SSL_CTX* ssl) {
+      if (ssl) {
+        util::http::TlsClient::FreeContext(ssl);
+      }
+    }
+  };
+
+  using SslPtr = std::unique_ptr<SSL_CTX, SslDeleter>;
+  void RunTask(SslPtr);
+
+  bool IsVersionOutdated(std::string_view remote, std::string_view current) const;
+
+  util::fb2::Fiber version_fiber_;
+  util::fb2::Done monitor_ver_done_;
+};
+
+}  // namespace dfly
diff --git a/tests/dragonfly/generic_test.py b/tests/dragonfly/generic_test.py
index 5d7c9f511..5dcf328dc 100644
--- a/tests/dragonfly/generic_test.py
+++ b/tests/dragonfly/generic_test.py
@@ -23,7 +23,7 @@ class TestKeys:
 @pytest.fixture(scope="function")
 def export_dfly_password() -> str:
     pwd = "flypwd"
-    with EnvironCntx(DFLY_PASSWORD=pwd):
+    with EnvironCntx(DFLY_requirepass=pwd):
         yield pwd