diff --git a/internal/nbconn/nbconn.go b/internal/nbconn/nbconn.go
index 6a92e8fb..0ceb3c79 100644
--- a/internal/nbconn/nbconn.go
+++ b/internal/nbconn/nbconn.go
@@ -1,4 +1,13 @@
 // Package nbconn implements a non-blocking net.Conn wrapper.
+//
+// It is designed to solve three problems.
+//
+// The first is resolving the deadlock that can occur when both sides of a connection are blocked writing because all
+// buffers between are full. See https://github.com/jackc/pgconn/issues/27 for discussion.
+//
+// The second is the inability to use a write deadline with a TLS.Conn without killing the connection.
+//
+// The third is to efficiently check if a connection has been closed via a non-blocking read.
 package nbconn
 
 import (
@@ -14,26 +23,38 @@ import (
 )
 
 var errClosed = errors.New("closed")
-var ErrWouldBlock = errors.New("would block")
+var ErrWouldBlock = new(wouldBlockError)
 
 const fakeNonblockingWaitDuration = 100 * time.Millisecond
 
-var NonBlockingDeadline = time.Date(1900, 1, 1, 0, 0, 0, 0, time.UTC)
+// NonBlockingDeadline is a magic value that when passed to Set[Read]Deadline places the connection in non-blocking read
+// mode.
+var NonBlockingDeadline = time.Date(1900, 1, 1, 0, 0, 0, 608536336, time.UTC)
 
-// Conn is a non-blocking net.Conn wrapper. It implements net.Conn.
-//
-// It is designed to solve three problems.
-//
-// The first is resolving the deadlock that can occur when both sides of a connection are blocked writing because all
-// buffers between are full. See https://github.com/jackc/pgconn/issues/27 for discussion.
-//
-// The second is the inability to use a write deadline with a TLS.Conn without killing the connection.
-//
-// The third is to efficiently check if a connection has been closed via a non-blocking read.
-type Conn struct {
-	netConn      net.Conn
-	tlsConn      *tls.Conn
-	maybeTLSConn net.Conn
+// disableSetDeadlineDeadline is a magic value that when passed to Set[Read|Write]Deadline causes those methods to
+// ignore all future calls.
+var disableSetDeadlineDeadline = time.Date(1900, 1, 1, 0, 0, 0, 968549727, time.UTC)
+
+// wouldBlockError implements net.Error so tls.Conn will recognize ErrWouldBlock as a temporary error.
+type wouldBlockError struct{}
+
+func (*wouldBlockError) Error() string {
+	return "would block"
+}
+
+func (*wouldBlockError) Timeout() bool   { return true }
+func (*wouldBlockError) Temporary() bool { return true }
+
+// Conn is a net.Conn where Write never blocks and always succeeds. Flush must be called to actually write to the
+// underlying connection.
+type Conn interface {
+	net.Conn
+	Flush() error
+}
+
+// NetConn is a non-blocking net.Conn wrapper. It implements net.Conn.
+type NetConn struct {
+	conn net.Conn
 
 	readQueue  bufferQueue
 	writeQueue bufferQueue
@@ -51,21 +72,14 @@ type Conn struct {
 	closed int64 // 0 = not closed, 1 = closed
 }
 
-func New(conn net.Conn) *Conn {
-	return &Conn{
-		netConn:      conn,
-		maybeTLSConn: conn,
+func NewNetConn(conn net.Conn) *NetConn {
+	return &NetConn{
+		conn: conn,
 	}
 }
 
-// StartTLS starts using TLS. It must not be called concurrently with any other method and must only be called once.
-func (c *Conn) StartTLS(config *tls.Config) {
-	c.tlsConn = tls.Client(c.netConn, config)
-	c.maybeTLSConn = c.tlsConn
-}
-
 // Read implements io.Reader.
-func (c *Conn) Read(b []byte) (n int, err error) {
+func (c *NetConn) Read(b []byte) (n int, err error) {
 	if c.isClosed() {
 		return 0, errClosed
 	}
@@ -106,7 +120,7 @@ func (c *Conn) Read(b []byte) (n int, err error) {
 	if readNonblocking {
 		readN, err = c.nonblockingRead(b[n:])
 	} else {
-		readN, err = c.maybeTLSConn.Read(b[n:])
+		readN, err = c.conn.Read(b[n:])
 	}
 	n += readN
 	return n, err
@@ -114,7 +128,7 @@ func (c *Conn) Read(b []byte) (n int, err error) {
 
 // Write implements io.Writer. It never blocks due to buffering all writes. It will only return an error if the Conn is
 // closed. Call Flush to actually write to the underlying connection.
-func (c *Conn) Write(b []byte) (n int, err error) {
+func (c *NetConn) Write(b []byte) (n int, err error) {
 	if c.isClosed() {
 		return 0, errClosed
 	}
@@ -125,14 +139,14 @@ func (c *Conn) Write(b []byte) (n int, err error) {
 	return len(b), nil
 }
 
-func (c *Conn) Close() (err error) {
+func (c *NetConn) Close() (err error) {
 	swapped := atomic.CompareAndSwapInt64(&c.closed, 0, 1)
 	if !swapped {
 		return errClosed
 	}
 
 	defer func() {
-		closeErr := c.maybeTLSConn.Close()
+		closeErr := c.conn.Close()
 		if err == nil {
 			err = closeErr
 		}
@@ -148,16 +162,16 @@ func (c *Conn) Close() (err error) {
 	return nil
 }
 
-func (c *Conn) LocalAddr() net.Addr {
-	return c.maybeTLSConn.LocalAddr()
+func (c *NetConn) LocalAddr() net.Addr {
+	return c.conn.LocalAddr()
 }
 
-func (c *Conn) RemoteAddr() net.Addr {
-	return c.maybeTLSConn.RemoteAddr()
+func (c *NetConn) RemoteAddr() net.Addr {
+	return c.conn.RemoteAddr()
 }
 
 // SetDeadline is the equivalent of calling SetReadDealine(t) and SetWriteDeadline(t).
-func (c *Conn) SetDeadline(t time.Time) error {
+func (c *NetConn) SetDeadline(t time.Time) error {
 	err := c.SetReadDeadline(t)
 	if err != nil {
 		return err
@@ -166,13 +180,20 @@ func (c *Conn) SetDeadline(t time.Time) error {
 }
 
 // SetReadDeadline sets the read deadline as t. If t == NonBlockingDeadline then future reads will be non-blocking.
-func (c *Conn) SetReadDeadline(t time.Time) error {
+func (c *NetConn) SetReadDeadline(t time.Time) error {
 	if c.isClosed() {
 		return errClosed
 	}
 
 	c.readDeadlineLock.Lock()
 	defer c.readDeadlineLock.Unlock()
+	if c.readDeadline == disableSetDeadlineDeadline {
+		return nil
+	}
+	if t == disableSetDeadlineDeadline {
+		c.readDeadline = t
+		return nil
+	}
 
 	if t == NonBlockingDeadline {
 		c.readNonblocking = true
@@ -183,22 +204,30 @@ func (c *Conn) SetReadDeadline(t time.Time) error {
 
 	c.readDeadline = t
 
-	return c.maybeTLSConn.SetReadDeadline(t)
+	return c.conn.SetReadDeadline(t)
 }
 
-func (c *Conn) SetWriteDeadline(t time.Time) error {
+func (c *NetConn) SetWriteDeadline(t time.Time) error {
 	if c.isClosed() {
 		return errClosed
 	}
 
 	c.writeDeadlineLock.Lock()
 	defer c.writeDeadlineLock.Unlock()
+	if c.writeDeadline == disableSetDeadlineDeadline {
+		return nil
+	}
+	if t == disableSetDeadlineDeadline {
+		c.writeDeadline = t
+		return nil
+	}
+
 	c.writeDeadline = t
 
-	return c.netConn.SetWriteDeadline(t)
+	return c.conn.SetWriteDeadline(t)
 }
 
-func (c *Conn) Flush() error {
+func (c *NetConn) Flush() error {
 	if c.isClosed() {
 		return errClosed
 	}
@@ -209,7 +238,7 @@ func (c *Conn) Flush() error {
 }
 
 // flush does the actual work of flushing the writeQueue. readFlushLock must already be held.
-func (c *Conn) flush() error {
+func (c *NetConn) flush() error {
 	var stopChan chan struct{}
 	var errChan chan error
 
@@ -255,7 +284,7 @@ func (c *Conn) flush() error {
 	return nil
 }
 
-func (c *Conn) bufferNonblockingRead() (stopChan chan struct{}, errChan chan error) {
+func (c *NetConn) bufferNonblockingRead() (stopChan chan struct{}, errChan chan error) {
 	stopChan = make(chan struct{})
 	errChan = make(chan error, 1)
 
@@ -286,28 +315,28 @@ func (c *Conn) bufferNonblockingRead() (stopChan chan struct{}, errChan chan err
 	return stopChan, errChan
 }
 
-func (c *Conn) isClosed() bool {
+func (c *NetConn) isClosed() bool {
 	closed := atomic.LoadInt64(&c.closed)
 	return closed == 1
 }
 
-func (c *Conn) nonblockingWrite(b []byte) (n int, err error) {
+func (c *NetConn) nonblockingWrite(b []byte) (n int, err error) {
 	return c.fakeNonblockingWrite(b)
 }
 
-func (c *Conn) fakeNonblockingWrite(b []byte) (n int, err error) {
+func (c *NetConn) fakeNonblockingWrite(b []byte) (n int, err error) {
 	c.writeDeadlineLock.Lock()
 	defer c.writeDeadlineLock.Unlock()
 
 	deadline := time.Now().Add(fakeNonblockingWaitDuration)
 	if c.writeDeadline.IsZero() || deadline.Before(c.writeDeadline) {
-		err = c.netConn.SetWriteDeadline(deadline)
+		err = c.conn.SetWriteDeadline(deadline)
 		if err != nil {
 			return 0, err
 		}
 		defer func() {
 			// Ignoring error resetting deadline as there is nothing that can reasonably be done if it fails.
-			c.netConn.SetWriteDeadline(c.writeDeadline)
+			c.conn.SetWriteDeadline(c.writeDeadline)
 
 			if err != nil {
 				if errors.Is(err, os.ErrDeadlineExceeded) {
@@ -317,26 +346,26 @@ func (c *Conn) fakeNonblockingWrite(b []byte) (n int, err error) {
 		}()
 	}
 
-	return c.netConn.Write(b)
+	return c.conn.Write(b)
 }
 
-func (c *Conn) nonblockingRead(b []byte) (n int, err error) {
+func (c *NetConn) nonblockingRead(b []byte) (n int, err error) {
 	return c.fakeNonblockingRead(b)
 }
 
-func (c *Conn) fakeNonblockingRead(b []byte) (n int, err error) {
+func (c *NetConn) fakeNonblockingRead(b []byte) (n int, err error) {
 	c.readDeadlineLock.Lock()
 	defer c.readDeadlineLock.Unlock()
 
 	deadline := time.Now().Add(fakeNonblockingWaitDuration)
 	if c.readDeadline.IsZero() || deadline.Before(c.readDeadline) {
-		err = c.netConn.SetReadDeadline(deadline)
+		err = c.conn.SetReadDeadline(deadline)
 		if err != nil {
 			return 0, err
 		}
 		defer func() {
 			// Ignoring error resetting deadline as there is nothing that can reasonably be done if it fails.
-			c.netConn.SetReadDeadline(c.readDeadline)
+			c.conn.SetReadDeadline(c.readDeadline)
 
 			if err != nil {
 				if errors.Is(err, os.ErrDeadlineExceeded) {
@@ -346,7 +375,58 @@ func (c *Conn) fakeNonblockingRead(b []byte) (n int, err error) {
 		}()
 	}
 
-	return c.netConn.Read(b)
+	return c.conn.Read(b)
 }
 
 // syscall.Conn is interface
+
+// TLSClient establishes a TLS connection as a client over conn using config.
+//
+// To avoid the first Read on the returned *TLSConn also triggering a Write due to the TLS handshake and thereby
+// potentially causing a read and write deadlines to behave unexpectedly, Handshake is called explicitly before the
+// *TLSConn is returned.
+func TLSClient(conn *NetConn, config *tls.Config) (*TLSConn, error) {
+	tc := tls.Client(conn, config)
+	err := tc.Handshake()
+	if err != nil {
+		return nil, err
+	}
+
+	// Ensure last written part of Handshake is actually sent.
+	err = conn.Flush()
+	if err != nil {
+		return nil, err
+	}
+
+	return &TLSConn{
+		tlsConn: tc,
+		nbConn:  conn,
+	}, nil
+}
+
+// TLSConn is a TLS wrapper around a *Conn. It works around a temporary write error (such as a timeout) being fatal to a
+// tls.Conn.
+type TLSConn struct {
+	tlsConn *tls.Conn
+	nbConn  *NetConn
+}
+
+func (tc *TLSConn) Read(b []byte) (n int, err error)  { return tc.tlsConn.Read(b) }
+func (tc *TLSConn) Write(b []byte) (n int, err error) { return tc.tlsConn.Write(b) }
+func (tc *TLSConn) Flush() error                      { return tc.nbConn.Flush() }
+func (tc *TLSConn) LocalAddr() net.Addr               { return tc.tlsConn.LocalAddr() }
+func (tc *TLSConn) RemoteAddr() net.Addr              { return tc.tlsConn.RemoteAddr() }
+
+func (tc *TLSConn) Close() error {
+	// tls.Conn.closeNotify() sets a 5 second deadline to avoid blocking, sends a TLS alert close notification, and then
+	// sets the deadline to now. This causes NetConn's Close not to be able to flush the write buffer. Instead we set our
+	// own 5 second deadline then make all set deadlines no-op.
+	tc.tlsConn.SetDeadline(time.Now().Add(time.Second * 5))
+	tc.tlsConn.SetDeadline(disableSetDeadlineDeadline)
+
+	return tc.tlsConn.Close()
+}
+
+func (tc *TLSConn) SetDeadline(t time.Time) error      { return tc.tlsConn.SetDeadline(t) }
+func (tc *TLSConn) SetReadDeadline(t time.Time) error  { return tc.tlsConn.SetReadDeadline(t) }
+func (tc *TLSConn) SetWriteDeadline(t time.Time) error { return tc.tlsConn.SetWriteDeadline(t) }
diff --git a/internal/nbconn/nbconn_test.go b/internal/nbconn/nbconn_test.go
index d3b56e36..8622fcff 100644
--- a/internal/nbconn/nbconn_test.go
+++ b/internal/nbconn/nbconn_test.go
@@ -65,7 +65,7 @@ pz01y53wMSTJs0ocAxkYvUc5laF+vMsLpG2vp8f35w8uKuO7+vm5LAjUsPd099jG
 2qWm8jTPeDC3sq+67s2oojHf+Q==
 -----END TESTING KEY-----`, "TESTING KEY", "PRIVATE KEY"))
 
-func testVariants(t *testing.T, f func(t *testing.T, local *nbconn.Conn, remote net.Conn)) {
+func testVariants(t *testing.T, f func(t *testing.T, local nbconn.Conn, remote net.Conn)) {
 	for _, tt := range []struct {
 		name      string
 		makeConns func(t *testing.T) (local, remote net.Conn)
@@ -89,16 +89,32 @@ func testVariants(t *testing.T, f func(t *testing.T, local *nbconn.Conn, remote
 	} {
 		t.Run(tt.name, func(t *testing.T) {
 			local, remote := tt.makeConns(t)
-			conn := nbconn.New(local)
+
+			var conn nbconn.Conn
+			netConn := nbconn.NewNetConn(local)
 
 			if tt.useTLS {
 				cert, err := tls.X509KeyPair(testTLSPublicKey, testTLSPrivateKey)
 				require.NoError(t, err)
 
-				remote = tls.Server(remote, &tls.Config{
+				tlsServer := tls.Server(remote, &tls.Config{
 					Certificates: []tls.Certificate{cert},
 				})
-				conn.StartTLS(&tls.Config{InsecureSkipVerify: true})
+				serverTLSHandshakeChan := make(chan error)
+				go func() {
+					err := tlsServer.Handshake()
+					serverTLSHandshakeChan <- err
+				}()
+
+				tlsConn, err := nbconn.TLSClient(netConn, &tls.Config{InsecureSkipVerify: true})
+				require.NoError(t, err)
+				conn = tlsConn
+
+				err = <-serverTLSHandshakeChan
+				require.NoError(t, err)
+				remote = tlsServer
+			} else {
+				conn = netConn
 			}
 
 			f(t, conn, remote)
@@ -147,7 +163,7 @@ func makeTCPConns(t *testing.T) (local, remote net.Conn) {
 }
 
 func TestWriteIsBuffered(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 		// net.Pipe is synchronous so the Write would block if not buffered.
 		writeBuf := []byte("test")
 		n, err := conn.Write(writeBuf)
@@ -169,7 +185,7 @@ func TestWriteIsBuffered(t *testing.T) {
 }
 
 func TestSetWriteDeadlineDoesNotBlockWrite(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 		err := conn.SetWriteDeadline(time.Now())
 		require.NoError(t, err)
 
@@ -181,7 +197,7 @@ func TestSetWriteDeadlineDoesNotBlockWrite(t *testing.T) {
 }
 
 func TestReadFlushesWriteBuffer(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 		writeBuf := []byte("test")
 		n, err := conn.Write(writeBuf)
 		require.NoError(t, err)
@@ -208,7 +224,7 @@ func TestReadFlushesWriteBuffer(t *testing.T) {
 }
 
 func TestCloseFlushesWriteBuffer(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 		writeBuf := []byte("test")
 		n, err := conn.Write(writeBuf)
 		require.NoError(t, err)
@@ -229,7 +245,7 @@ func TestCloseFlushesWriteBuffer(t *testing.T) {
 }
 
 func TestNonBlockingRead(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 		err := conn.SetReadDeadline(nbconn.NonBlockingDeadline)
 		require.NoError(t, err)
 
@@ -254,7 +270,7 @@ func TestNonBlockingRead(t *testing.T) {
 }
 
 func TestReadPreviouslyBuffered(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 
 		errChan := make(chan error, 1)
 		go func() {
@@ -291,7 +307,7 @@ func TestReadPreviouslyBuffered(t *testing.T) {
 }
 
 func TestReadPreviouslyBufferedPartialRead(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 
 		errChan := make(chan error, 1)
 		go func() {
@@ -334,7 +350,7 @@ func TestReadPreviouslyBufferedPartialRead(t *testing.T) {
 }
 
 func TestReadMultiplePreviouslyBuffered(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 		errChan := make(chan error, 1)
 		go func() {
 			err := func() error {
@@ -367,7 +383,7 @@ func TestReadMultiplePreviouslyBuffered(t *testing.T) {
 		require.NoError(t, err)
 
 		readBuf := make([]byte, 9)
-		n, err := conn.Read(readBuf)
+		n, err := io.ReadFull(conn, readBuf)
 		require.NoError(t, err)
 		require.EqualValues(t, 9, n)
 		require.Equal(t, []byte("alphabeta"), readBuf)
@@ -375,7 +391,7 @@ func TestReadMultiplePreviouslyBuffered(t *testing.T) {
 }
 
 func TestReadPreviouslyBufferedAndReadMore(t *testing.T) {
-	testVariants(t, func(t *testing.T, conn *nbconn.Conn, remote net.Conn) {
+	testVariants(t, func(t *testing.T, conn nbconn.Conn, remote net.Conn) {
 
 		flushCompleteChan := make(chan struct{})
 		errChan := make(chan error, 1)
diff --git a/pgconn/pgconn.go b/pgconn/pgconn.go
index bac08db0..5a5fac82 100644
--- a/pgconn/pgconn.go
+++ b/pgconn/pgconn.go
@@ -230,13 +230,14 @@ func connect(ctx context.Context, config *Config, fallbackConfig *FallbackConfig
 		}
 		return nil, &connectError{config: config, msg: "dial error", err: err}
 	}
+	netConn = nbconn.NewNetConn(netConn)
 
 	pgConn.conn = netConn
 	pgConn.contextWatcher = newContextWatcher(netConn)
 	pgConn.contextWatcher.Watch(ctx)
 
 	if fallbackConfig.TLSConfig != nil {
-		tlsConn, err := startTLS(netConn, fallbackConfig.TLSConfig)
+		tlsConn, err := startTLS(netConn.(*nbconn.NetConn), fallbackConfig.TLSConfig)
 		pgConn.contextWatcher.Unwatch() // Always unwatch `netConn` after TLS.
 		if err != nil {
 			netConn.Close()
@@ -248,11 +249,6 @@ func connect(ctx context.Context, config *Config, fallbackConfig *FallbackConfig
 		pgConn.contextWatcher.Watch(ctx)
 	}
 
-	pgConn.conn = nbconn.New(pgConn.conn)
-	pgConn.contextWatcher.Unwatch() // context watcher should watch nbconn
-	pgConn.contextWatcher = newContextWatcher(pgConn.conn)
-	pgConn.contextWatcher.Watch(ctx)
-
 	defer pgConn.contextWatcher.Unwatch()
 
 	pgConn.parameterStatuses = make(map[string]string)
@@ -357,7 +353,7 @@ func newContextWatcher(conn net.Conn) *ctxwatch.ContextWatcher {
 	)
 }
 
-func startTLS(conn net.Conn, tlsConfig *tls.Config) (net.Conn, error) {
+func startTLS(conn *nbconn.NetConn, tlsConfig *tls.Config) (net.Conn, error) {
 	err := binary.Write(conn, binary.BigEndian, []int32{8, 80877103})
 	if err != nil {
 		return nil, err
@@ -372,7 +368,12 @@ func startTLS(conn net.Conn, tlsConfig *tls.Config) (net.Conn, error) {
 		return nil, errors.New("server refused TLS connection")
 	}
 
-	return tls.Client(conn, tlsConfig), nil
+	tlsConn, err := nbconn.TLSClient(conn, tlsConfig)
+	if err != nil {
+		return nil, err
+	}
+
+	return tlsConn, nil
 }
 
 func (pgConn *PgConn) txPasswordMessage(password string) (err error) {