diff --git a/dnscrypt-proxy/config.go b/dnscrypt-proxy/config.go
index 49dc6d07cd..757e14189f 100644
--- a/dnscrypt-proxy/config.go
+++ b/dnscrypt-proxy/config.go
@@ -18,8 +18,7 @@ import (
 )
 
 const (
-	MaxTimeout             = 3600
-	DefaultNetprobeAddress = "9.9.9.9:53"
+	MaxTimeout = time.Hour
 )
 
 type Config struct {
@@ -95,7 +94,8 @@ type Config struct {
 	TLSCipherSuite           []uint16                    `toml:"tls_cipher_suite"`
 	TLSPreferRSA             bool                        `toml:"tls_prefer_rsa"`
 	TLSKeyLogFile            string                      `toml:"tls_key_log_file"`
-	NetprobeAddress          string                      `toml:"netprobe_address"`
+	NetprobeAddresses        []string                    `toml:"netprobe_addresses"`
+	NetprobeAddressLegacy    string                      `toml:"netprobe_address"`
 	NetprobeTimeout          int                         `toml:"netprobe_timeout"`
 	OfflineMode              bool                        `toml:"offline_mode"`
 	HTTPProxyURL             string                      `toml:"http_proxy"`
@@ -777,3 +777,11 @@ func isIPAndPort(addrStr string) error {
 	}
 	return nil
 }
+
+func GetDefaultNetprobeAddresses() ([]string) {
+	return []string{
+		"[2620:fe::fe]:53",
+		"9.9.9.9:53",
+	}
+}
+
diff --git a/dnscrypt-proxy/config_loader.go b/dnscrypt-proxy/config_loader.go
index 60e76746ee..b19062cb43 100644
--- a/dnscrypt-proxy/config_loader.go
+++ b/dnscrypt-proxy/config_loader.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"context"
 	"errors"
 	"flag"
 	"fmt"
@@ -8,12 +9,14 @@ import (
 	"net/http"
 	"net/url"
 	"os"
+	"slices"
 	"strconv"
 	"strings"
 	"time"
 
 	"github.com/jedisct1/dlog"
 	stamps "github.com/jedisct1/go-dnsstamps"
+	"github.com/projectdiscovery/utils/slice"
 	netproxy "golang.org/x/net/proxy"
 )
 
@@ -463,23 +466,56 @@ func configureSourceRestrictions(proxy *Proxy, flags *ConfigFlags, config *Confi
 	proxy.SourceODoH = config.SourceODoH
 }
 
-// determineNetprobeAddress - Determines the address to use for network probing
-func determineNetprobeAddress(flags *ConfigFlags, config *Config) (string, int) {
-	netprobeTimeout := config.NetprobeTimeout
+// determineNetprobeAddresses - Determines the addresses to use for network probing
+func determineNetprobeAddresses(
+	flags *ConfigFlags,
+	config *Config,
+) ([]string, time.Duration) {
+	netprobeTimeout := time.Duration(config.NetprobeTimeout) * time.Second
 	flag.Visit(func(commandLineFlag *flag.Flag) {
 		if commandLineFlag.Name == "netprobe-timeout" && flags.NetprobeTimeoutOverride != nil {
-			netprobeTimeout = *flags.NetprobeTimeoutOverride
+			netprobeTimeout = time.Duration(*flags.NetprobeTimeoutOverride) * time.Second
 		}
 	})
 
-	netprobeAddress := DefaultNetprobeAddress
-	if len(config.NetprobeAddress) > 0 {
-		netprobeAddress = config.NetprobeAddress
-	} else if len(config.BootstrapResolvers) > 0 {
-		netprobeAddress = config.BootstrapResolvers[0]
+	if netprobeTimeout < 0 || netprobeTimeout > MaxTimeout {
+		netprobeTimeout = MaxTimeout
 	}
 
-	return netprobeAddress, netprobeTimeout
+	netprobeAddresses := slices.Clone(config.NetprobeAddresses)
+
+	if len(config.NetprobeAddressLegacy) > 0 {
+		if len(netprobeAddresses) <= 0 {
+			dlog.Warn(
+				"netprobe_address was changed to a netprobe_addresses, a list -- Please update your configuration",
+			)
+			netprobeAddresses = append(netprobeAddresses, config.NetprobeAddressLegacy)
+		} else {
+			dlog.Fatal(
+				"Can't use a list of netprobe_addresses at the same time as a netprobe_address",
+			)
+
+		}
+	}
+
+	if len(netprobeAddresses) <= 0 && len(config.BootstrapResolvers) > 0 {
+		netprobeAddresses = append(
+			netprobeAddresses,
+			config.BootstrapResolvers...,
+		)
+	}
+
+	if len(netprobeAddresses) <= 0 {
+		netprobeAddresses = append(
+			netprobeAddresses,
+			GetDefaultNetprobeAddresses()...,
+		)
+	}
+
+	netprobeAddresses = sliceutil.Dedupe(netprobeAddresses)
+
+
+	return netprobeAddresses, netprobeTimeout
 }
 
 // initializeNetworking - Initializes networking
@@ -489,8 +525,15 @@ func initializeNetworking(proxy *Proxy, flags *ConfigFlags, config *Config) erro
 		return nil
 	}
 
-	netprobeAddress, netprobeTimeout := determineNetprobeAddress(flags, config)
-	if err := NetProbe(proxy, netprobeAddress, netprobeTimeout); err != nil {
+	netprobeAddresses, netprobeTimeout := determineNetprobeAddresses(flags, config)
+
+	ctx, cancel := context.WithTimeout(context.Background(), netprobeTimeout)
+	defer cancel()
+	if err := NetProbe(
+		proxy,
+		netprobeAddresses,
+		ctx,
+	); err != nil {
 		return err
 	}
 
diff --git a/dnscrypt-proxy/example-dnscrypt-proxy.toml b/dnscrypt-proxy/example-dnscrypt-proxy.toml
index b9e4b73cdc..30cc546b07 100644
--- a/dnscrypt-proxy/example-dnscrypt-proxy.toml
+++ b/dnscrypt-proxy/example-dnscrypt-proxy.toml
@@ -373,7 +373,7 @@ ignore_system_dns = true
 
 netprobe_timeout = 60
 
-## Address and port to try initializing a connection to, just to check
+## Address and port pairs to try initializing a connection to, just to check
 ## if the network is up. It can be any address and any port, even if
 ## there is nothing answering these on the other side. Just don't use
 ## a local address, as the goal is to check for Internet connectivity.
@@ -382,7 +382,11 @@ netprobe_timeout = 60
 ## On other operating systems, the connection will be initialized
 ## but nothing will be sent at all.
 
-netprobe_address = '9.9.9.9:53'
+
+netprobe_addresses = [
+	'[2620:fe::fe]:53',
+	'9.9.9.9:53',
+]
 
 
 ## Offline mode - Do not use any remote encrypted servers.
diff --git a/dnscrypt-proxy/netprobe.go b/dnscrypt-proxy/netprobe.go
new file mode 100644
index 0000000000..7e8cb19249
--- /dev/null
+++ b/dnscrypt-proxy/netprobe.go
@@ -0,0 +1,220 @@
+package main
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net"
+	"runtime"
+	"time"
+
+	"github.com/jedisct1/dlog"
+)
+
+// determineNetprobeIntervals - Determines an interval that should finish at least margin before deadline
+//
+// mostly useful with a context.Context deadline
+func determineNetprobeIntervals(
+	ideal time.Duration,
+	deadline time.Time,
+	margin time.Duration,
+) (interval time.Duration, count int, ok bool) {
+	remaining := time.Until(deadline) - margin
+
+	if ideal <= 0 || remaining <= 0 {
+		return 0, 0, false
+	}
+
+	// Smallest number of intervals that does not require
+	// an interval larger than the ideal.
+	count = int((remaining + ideal - 1) / ideal)
+
+	interval = remaining / time.Duration(count)
+
+	if interval <= 0 {
+		return 0, 0, false
+	}
+
+	return interval, count, true
+}
+
+func NetProbe(
+	proxy *Proxy,
+	hosts_port []string,
+	ctx context.Context,
+) error {
+	if len(hosts_port) == 0 || ctx.Err() != nil {
+		return nil
+	}
+	if captivePortalHandler, err := ColdStart(proxy); err == nil {
+		if captivePortalHandler != nil {
+			defer captivePortalHandler.Stop()
+		}
+	} else {
+		dlog.Critical(err)
+	}
+
+
+	ctx, cancelDial := context.WithCancel(ctx)
+	defer cancelDial()
+
+	type result struct {
+		host string
+		ok   bool
+		err  error
+	}
+
+	results := make(chan result, len(hosts_port))
+
+	var probesPending int = 0
+	for _, host := range hosts_port {
+		if len(host) <= 0 {
+			continue
+		}
+
+		probesPending++
+		go func(host string) {
+			ok, err := NetProbeSingle(proxy, host, ctx)
+			results <- result{
+				host: host,
+				ok:   ok,
+				err:  err,
+			}
+			if ok {
+				cancelDial()
+			}
+		}(host)
+	}
+	if probesPending <= 0 {
+		dlog.Error(
+			"netprobe_addresses non-zero length but all addresses are invalid somehow",
+		)
+		return nil
+	}
+
+	for {
+		select {
+		case res := <-results:
+			if res.ok && res.err == nil {
+				dlog.Noticef(
+					"Network connectivity detected (%s)",
+					res.host,
+				)
+				return nil
+			} else if !errors.Is(res.err, context.Canceled) &&
+					  !errors.Is(res.err, context.DeadlineExceeded) {
+				dlog.Noticef("(%s) %v", res.host, res.err)
+			}
+
+			probesPending--
+			if probesPending <= 0 {
+				dlog.Error("Timeout while waiting for network connectivity")
+				return nil
+			}
+
+		}
+	}
+}
+
+func NetProbeSingle(
+	proxy *Proxy,
+	host_port string,
+	ctx context.Context,
+) (ok bool, err error) {
+	if len(host_port) <= 0 {
+		return false, nil
+	}
+	if ctx.Err() != nil {
+		return false, ctx.Err()
+	}
+	if _, _, err := net.SplitHostPort(host_port); err != nil {
+		return false, err
+	}
+
+	loggedMessages := make(map[string]struct{})
+
+	dialer := net.Dialer{
+		Timeout: proxy.timeout,
+	}
+
+	deadline, deadlineOk := ctx.Deadline()
+
+	interval := time.Second
+
+	if deadlineOk {
+		if i, _, ok := determineNetprobeIntervals(
+			time.Second,
+			deadline,
+			10*time.Millisecond,
+		); ok {
+			interval = i
+		}
+	}
+
+	for {
+		retryLimitTimer := time.NewTimer(interval)
+
+		pc, err := dialer.DialContext(
+			ctx,
+			"udp",
+			host_port,
+		)
+		if runtime.GOOS == "windows" && err == nil {
+			// Write at least 1 byte. This ensures that sockets are ready to use for writing.
+			// Windows specific: during the system startup, sockets can be created but the underlying buffers may not be
+			// set up yet. If this is the case Write fails with WSAENOBUFS: "An operation on a socket could not be
+			// performed because the system lacked sufficient buffer space or because a queue was full"
+			_, err = pc.Write([]byte{0})
+			if err != nil {
+				pc.Close()
+			}
+		}
+
+		if err != nil {
+			msg := ""
+			var dnsErr *net.DNSError
+
+			switch {
+			case ctx.Err() != nil:
+				msg = ""
+			case errors.As(err, &dnsErr):
+				msg = fmt.Sprintf(
+					"(%s) Name resolution error: %v",
+					host_port,
+					dnsErr,
+				)
+			default:
+				msg = fmt.Sprintf(
+					"(%s) Network not available yet -- waiting...",
+					host_port,
+				)
+			}
+
+
+			if _, exists := loggedMessages[msg]; !exists && msg != "" {
+				dlog.Notice(msg)
+				loggedMessages[msg] = struct{}{}
+			}
+
+			dlog.Debugf(
+				"(%s) %v",
+				host_port,
+				err,
+			)
+
+			select {
+			case <-ctx.Done():
+				dlog.Debugf(
+					"(%s) context done",
+					host_port,
+				)
+				return false, ctx.Err()
+			case <-retryLimitTimer.C:
+			}
+
+			continue
+		}
+		pc.Close()
+		return true, nil
+	}
+}
diff --git a/dnscrypt-proxy/netprobe_others.go b/dnscrypt-proxy/netprobe_others.go
deleted file mode 100644
index 81217f9655..0000000000
--- a/dnscrypt-proxy/netprobe_others.go
+++ /dev/null
@@ -1,50 +0,0 @@
-//go:build !windows
-
-package main
-
-import (
-	"net"
-	"time"
-
-	"github.com/jedisct1/dlog"
-)
-
-func NetProbe(proxy *Proxy, address string, timeout int) error {
-	if len(address) <= 0 || timeout == 0 {
-		return nil
-	}
-	if captivePortalHandler, err := ColdStart(proxy); err == nil {
-		if captivePortalHandler != nil {
-			defer captivePortalHandler.Stop()
-		}
-	} else {
-		dlog.Critical(err)
-	}
-	remoteUDPAddr, err := net.ResolveUDPAddr("udp", address)
-	if err != nil {
-		return err
-	}
-	retried := false
-	if timeout < 0 {
-		timeout = MaxTimeout
-	} else {
-		timeout = Min(MaxTimeout, timeout)
-	}
-	for tries := timeout; tries > 0; tries-- {
-		pc, err := net.DialTimeout("udp", remoteUDPAddr.String(), proxy.timeout)
-		if err != nil {
-			if !retried {
-				retried = true
-				dlog.Notice("Network not available yet -- waiting...")
-			}
-			dlog.Debug(err)
-			time.Sleep(1 * time.Second)
-			continue
-		}
-		pc.Close()
-		dlog.Notice("Network connectivity detected")
-		return nil
-	}
-	dlog.Error("Timeout while waiting for network connectivity")
-	return nil
-}
diff --git a/dnscrypt-proxy/netprobe_windows.go b/dnscrypt-proxy/netprobe_windows.go
deleted file mode 100644
index 5a63dfd2bf..0000000000
--- a/dnscrypt-proxy/netprobe_windows.go
+++ /dev/null
@@ -1,58 +0,0 @@
-package main
-
-import (
-	"net"
-	"time"
-
-	"github.com/jedisct1/dlog"
-)
-
-func NetProbe(proxy *Proxy, address string, timeout int) error {
-	if len(address) <= 0 || timeout == 0 {
-		return nil
-	}
-	if captivePortalHandler, err := ColdStart(proxy); err == nil {
-		if captivePortalHandler != nil {
-			defer captivePortalHandler.Stop()
-		}
-	} else {
-		dlog.Critical(err)
-	}
-	remoteUDPAddr, err := net.ResolveUDPAddr("udp", address)
-	if err != nil {
-		return err
-	}
-	retried := false
-	if timeout < 0 {
-		timeout = MaxTimeout
-	} else {
-		timeout = Min(MaxTimeout, timeout)
-	}
-	for tries := timeout; tries > 0; tries-- {
-		pc, err := net.DialTimeout("udp", remoteUDPAddr.String(), proxy.timeout)
-		if err == nil {
-			// Write at least 1 byte. This ensures that sockets are ready to use for writing.
-			// Windows specific: during the system startup, sockets can be created but the underlying buffers may not be
-			// set up yet. If this is the case Write fails with WSAENOBUFS: "An operation on a socket could not be
-			// performed because the system lacked sufficient buffer space or because a queue was full"
-			_, err = pc.Write([]byte{0})
-			if err != nil {
-				pc.Close()
-			}
-		}
-		if err != nil {
-			if !retried {
-				retried = true
-				dlog.Notice("Network not available yet -- waiting...")
-			}
-			dlog.Debug(err)
-			time.Sleep(1 * time.Second)
-			continue
-		}
-		pc.Close()
-		dlog.Notice("Network connectivity detected")
-		return nil
-	}
-	dlog.Error("Timeout while waiting for network connectivity")
-	return nil
-}
diff --git a/go.mod b/go.mod
index 407ede54d5..2f4d92ba7d 100644
--- a/go.mod
+++ b/go.mod
@@ -35,6 +35,8 @@ require (
 
 require (
 	github.com/hashicorp/go-syslog v1.0.0 // indirect
+	github.com/projectdiscovery/blackrock v0.0.2 // indirect
+	github.com/projectdiscovery/utils v0.11.2 // indirect
 	github.com/hashicorp/golang-lru/v2 v2.0.7 // indirect
 	github.com/quic-go/qpack v0.6.0 // indirect
 	go.uber.org/mock v0.6.0 // indirect
diff --git a/go.sum b/go.sum
index b8877ef106..8c78e1eecf 100644
--- a/go.sum
+++ b/go.sum
@@ -52,6 +52,10 @@ github.com/miekg/dns v1.1.72 h1:vhmr+TF2A3tuoGNkLDFK9zi36F2LS+hKTRW0Uf8kbzI=
 github.com/miekg/dns v1.1.72/go.mod h1:+EuEPhdHOsfk6Wk5TT2CzssZdqkmFhf8r+aVyDEToIs=
 github.com/powerman/check v1.13.0 h1:/uNADrvWRzsRKCN00LEN/Ph0XMlUmtOhZTw2Qr60nNQ=
 github.com/powerman/check v1.13.0/go.mod h1:h7WkuVUhfVN1yl/F6zm+zbZLeOUtx34+JpMA8aA2vR0=
+github.com/projectdiscovery/blackrock v0.0.2 h1:mxXdu0uM8P2L2Qi210COlU8QiICPFW/Rxk5QUhlPO2k=
+github.com/projectdiscovery/blackrock v0.0.2/go.mod h1:ANUtjDfaVrqB453bzToU+YB4cUbvBRpLvEwoWIwlTss=
+github.com/projectdiscovery/utils v0.11.2 h1:gfvXFBEHN4DgX8HBRzsoO1s2wH/2R+cH17cLpC865x4=
+github.com/projectdiscovery/utils v0.11.2/go.mod h1:HMxhxLigsAr+M9Oa8n9Z0ROZcs8wAJHGsgR7UGb+oUE=
 github.com/quic-go/go-ossfuzz-seeds v0.1.0 h1:APacT+iIaNF6fd8AGEiN3bT/Jtkd2jz4v4TzM7MFjy0=
 github.com/quic-go/go-ossfuzz-seeds v0.1.0/go.mod h1:3IOHRbJIc+L6YKMwfDtJAM9Vj9k0YY4muhuyUYk5tbk=
 github.com/quic-go/qpack v0.6.0 h1:g7W+BMYynC1LbYLSqRt8PBg5Tgwxn214ZZR34VIOjz8=