diff --git a/oyoyo/client.py b/oyoyo/client.py
index 6956d9b..e831bf0 100644
--- a/oyoyo/client.py
+++ b/oyoyo/client.py
@@ -39,6 +39,11 @@ except ImportError:
             "Pesterchum might not be able to validate certificates unless "
             "Python's root certs are installed."
         )
+    else:
+        PchumLog.info(
+            "Failed to import certifi, Pesterchum will not be able to validate "
+            "certificates if the system-provided root certificates are invalid."
+        )
 
 
 class IRCClientError(Exception):
@@ -200,45 +205,49 @@ class IRCClient:
                 # raise se
                 self._end = True  # This ok?
 
+    def get_ssl_context(self):
+        """Returns an SSL context for connecting over SSL/TLS.
+        Loads the certifi certs instead of the system-provided certificates if
+        the system certificate store is empty."""
+        context = ssl.create_default_context()
+        # Check if store is empty
+        empty_cert_store = list(context.cert_store_stats().values()).count(0) == 3
+        if empty_cert_store and "certifi" in sys.modules:
+            # Can't validate certificates if store is empty,
+            # load root certificates from certifi instead.
+            context = ssl.create_default_context(cafile=certifi.where())
+            PchumLog.info(
+                "Using SSL/TLS context with certifi-provided root certificates."
+            )
+        else:
+            PchumLog.info(
+                "Using SSL/TLS context with system-provided root certificates."
+            )
+        return context
+
     def connect(self, verify_hostname=True):
-        """initiates the connection to the server set in self.host:self.port"""
+        """initiates the connection to the server set in self.host:self.port
+        self.ssl decides whether the connection uses ssl.
+
+        Certificate validation when using SSL/TLS may be disabled by
+        passing the 'verify_hostname' parameter. The user is asked if they
+        want to disable it if this functions raises a certificate validation error,
+        in which case the function may be called again with 'verify_hostname'."""
         PchumLog.info("connecting to %s:%s" % (self.host, self.port))
 
-        if self.ssl == True:
-            context = ssl.create_default_context()
-            if verify_hostname == False:
-                context.check_hostname = False
-                context.verify_mode = ssl.CERT_NONE
-            else:
-                # Also load certifi provided root certs if present. (Mainly useful for MacOS)
-                if "certifi" in sys.modules:
-                    try:
-                        context.load_verify_locations(cafile=certifi.where())
-                    except:
-                        PchumLog.exception("")
+        # Open connection
+        plaintext_socket = socket.create_connection((self.host, self.port))
 
-            bare_sock = socket.create_connection((self.host, self.port))
+        if self.ssl:
+            # Upgrade connection to use SSL/TLS if enabled
+            context = self.get_ssl_context()
+            context.check_hostname = verify_hostname
             self.socket = context.wrap_socket(
-                bare_sock, server_hostname=self.host, do_handshake_on_connect=False
+                plaintext_socket, server_hostname=self.host
             )
-            while True:
-                try:
-                    self.socket.do_handshake()
-                    break
-                except ssl.SSLWantReadError:
-                    select.select([self.socket], [], [])
-                except ssl.SSLWantWriteError:
-                    select.select([], [self.socket], [])
-                except ssl.SSLCertVerificationError as e:
-                    # Disconnect for now
-                    self.socket.close()
-                    bare_sock.close()
-                    raise e
-
-            PchumLog.info("secure sockets version is %s" % self.socket.version())
-
         else:
-            self.socket = socket.create_connection((self.host, self.port))
+            # SSL/TLS is disabled, connection is plaintext
+            self.socket = plaintext_socket
 
         # setblocking is a shorthand for timeout,
         # we shouldn't use both.
@@ -249,17 +258,6 @@ class IRCClient:
         elif self.blocking:
             self.socket.setblocking(True)
 
-        # try:
-        #    self.socket.setsockopt(socket.SOL_SOCKET, socket.SO_KEEPALIVE, 1)
-        #    if hasattr(socket, "TCP_KEEPIDLE"):
-        #        self.socket.setsockopt(socket.IPPROTO_TCP, socket.TCP_KEEPIDLE, 1)
-        #    if hasattr(socket, "TCP_KEEPINTVL"):
-        #        self.socket.setsockopt(socket.IPPROTO_TCP, socket.TCP_KEEPINTVL, 1)
-        #    if hasattr(socket, "TCP_KEEPCNT"):
-        #        self.socket.setsockopt(socket.IPPROTO_TCP, socket.TCP_KEEPCNT, 1)
-        # except Exception as e:
-        #    print(e)
-
         helpers.nick(self, self.nick)
         helpers.user(self, self.username, self.realname)
         if self.connect_cb: