diff --git a/cmd/cloudflared/flags/flags.go b/cmd/cloudflared/flags/flags.go
index f31ff60e..89eadd8a 100644
--- a/cmd/cloudflared/flags/flags.go
+++ b/cmd/cloudflared/flags/flags.go
@@ -126,6 +126,9 @@ const (
 	// NoPrechecks is the command line flag to skip connectivity pre-checks at startup.
 	NoPrechecks = "no-prechecks"
 
+	// Prechecks is the command line flag to run connectivity pre-checks at startup.
+	Prechecks = "prechecks"
+
 	// LogLevel is the command line flag for the cloudflared logging level
 	LogLevel = "loglevel"
 
diff --git a/cmd/cloudflared/tunnel/cmd.go b/cmd/cloudflared/tunnel/cmd.go
index 16270980..f37e76fd 100644
--- a/cmd/cloudflared/tunnel/cmd.go
+++ b/cmd/cloudflared/tunnel/cmd.go
@@ -4,6 +4,7 @@ import (
 	"bufio"
 	"context"
 	"fmt"
+	"net"
 	"net/url"
 	"os"
 	"path/filepath"
@@ -31,11 +32,13 @@ import (
 	"github.com/cloudflare/cloudflared/credentials"
 	"github.com/cloudflare/cloudflared/diagnostic"
 	"github.com/cloudflare/cloudflared/edgediscovery"
+	"github.com/cloudflare/cloudflared/edgediscovery/allregions"
 	"github.com/cloudflare/cloudflared/ingress"
 	"github.com/cloudflare/cloudflared/logger"
 	"github.com/cloudflare/cloudflared/management"
 	"github.com/cloudflare/cloudflared/metrics"
 	"github.com/cloudflare/cloudflared/orchestration"
+	"github.com/cloudflare/cloudflared/prechecks"
 	"github.com/cloudflare/cloudflared/signal"
 	"github.com/cloudflare/cloudflared/supervisor"
 	"github.com/cloudflare/cloudflared/tlsconfig"
@@ -372,6 +375,17 @@ func StartServer(
 	info.Log(log)
 	logClientOptions(c, log)
 
+	// Run connectivity pre-checks for cloudflared. This runs in a separate
+	// goroutine, as we want to keep initializing cloudflared while prechecks
+	// are running.
+	if c.Bool(cfdflags.Prechecks) && !c.Bool(cfdflags.NoPrechecks) {
+		resolvedRegion := c.String(cfdflags.Region)
+		if resolvedRegion == "" && namedTunnel != nil {
+			resolvedRegion = namedTunnel.Credentials.Endpoint
+		}
+		go runPrechecks(c, log, resolvedRegion)
+	}
+
 	// this context drives the server, when it's canceled tunnel and all other components (origins, dns, etc...) should stop
 	ctx, cancel := context.WithCancel(c.Context)
 	defer cancel()
@@ -513,6 +527,49 @@ func StartServer(
 	return waitToShutdown(&wg, cancel, errC, graceShutdownC, gracePeriod, log)
 }
 
+// runPrechecks executes connectivity pre-checks and logs the results.
+// Pre-checks are diagnostic only and do not gate tunnel startup.
+func runPrechecks(c *cli.Context, log *zerolog.Logger, region string) {
+	ipVersion := allregions.Auto
+	if ipVersionStr := c.String(cfdflags.EdgeIpVersion); ipVersionStr != "" {
+		parsedVersion, err := parseConfigIPVersion(ipVersionStr)
+		if err == nil {
+			ipVersion = parsedVersion
+		} else {
+			log.Warn().Str("edgeIpVersion", ipVersionStr).Err(err).Msg("Invalid edge-ip-version value, using auto")
+		}
+	}
+
+	cfg := prechecks.Config{
+		Region:    region,
+		IPVersion: ipVersion,
+	}
+
+	// Mirror the static/dynamic edge selection from supervisor/supervisor.go:
+	// when --edge addresses are provided, bypass DNS discovery entirely.
+	var dnsResolver prechecks.DNSResolver
+	if edgeAddrs := c.StringSlice(cfdflags.Edge); len(edgeAddrs) > 0 {
+		dnsResolver = &prechecks.StaticEdgeDNSResolver{Addrs: edgeAddrs, Log: log}
+	} else {
+		dnsResolver = &prechecks.EdgeDNSResolver{Log: log}
+	}
+
+	dialers := prechecks.RunDialers{
+		DNSResolver:      dnsResolver,
+		TCPDialer:        &prechecks.EdgeTCPDialer{},
+		QUICDialer:       &prechecks.EdgeQUICDialer{},
+		ManagementDialer: &prechecks.NetManagementDialer{Dialer: net.Dialer{}},
+	}
+
+	report := prechecks.Run(c.Context, c.String(cfdflags.CACert), cfg, log, dialers)
+
+	// Output the human-readable table to console
+	fmt.Println(report.String())
+
+	// Also log structured results for log aggregation
+	report.LogEvent(log)
+}
+
 func waitToShutdown(wg *sync.WaitGroup,
 	cancelServerContext func(),
 	errC <-chan error,
@@ -889,6 +946,13 @@ func configureCloudflaredFlags(shouldHide bool) []cli.Flag {
 			Value:   false,
 			Hidden:  shouldHide,
 		}),
+		altsrc.NewBoolFlag(&cli.BoolFlag{
+			Name:    cfdflags.Prechecks,
+			Usage:   "Run connectivity pre-checks at startup.",
+			EnvVars: []string{"TUNNEL_PRECHECKS"},
+			Value:   false,
+			Hidden:  shouldHide,
+		}),
 		altsrc.NewStringFlag(&cli.StringFlag{
 			Name:  cfdflags.Metrics,
 			Value: metrics.GetMetricsDefaultAddress(metrics.Runtime),
diff --git a/cmd/cloudflared/tunnel/configuration.go b/cmd/cloudflared/tunnel/configuration.go
index 96283906..225da347 100644
--- a/cmd/cloudflared/tunnel/configuration.go
+++ b/cmd/cloudflared/tunnel/configuration.go
@@ -262,6 +262,7 @@ func prepareTunnelConfig(
 		QUICConnectionLevelFlowControlLimit: c.Uint64(flags.QuicConnLevelFlowControlLimit),
 		QUICStreamLevelFlowControlLimit:     c.Uint64(flags.QuicStreamLevelFlowControlLimit),
 		NoPrechecks:                         c.Bool(flags.NoPrechecks),
+		Prechecks:                           c.Bool(flags.Prechecks),
 		OriginDNSService:                    dnsService,
 		OriginDialerService:                 originDialerService,
 	}
diff --git a/cmd/cloudflared/tunnel/subcommands.go b/cmd/cloudflared/tunnel/subcommands.go
index b3a2198d..ff46acd5 100644
--- a/cmd/cloudflared/tunnel/subcommands.go
+++ b/cmd/cloudflared/tunnel/subcommands.go
@@ -489,7 +489,7 @@ func readyCommand(c *cli.Context) error {
 	if err != nil {
 		return err
 	}
-	// nolint: gosec
+	// nolint: gosec // URL is constructed from the user-configured local metrics endpoint.
 	res, err := http.DefaultClient.Do(req)
 	if err != nil {
 		return err
@@ -1109,6 +1109,7 @@ func diagCommand(ctx *cli.Context) error {
 		Address:        sctx.c.String(flags.Metrics),
 		ContainerID:    sctx.c.String(diagContainerIDFlagName),
 		PodID:          sctx.c.String(diagPodFlagName),
+		Region:         sctx.c.String(flags.Region),
 		Toggles: diagnostic.Toggles{
 			NoDiagLogs:    sctx.c.Bool(noDiagLogsFlagName),
 			NoDiagMetrics: sctx.c.Bool(noDiagMetricsFlagName),
diff --git a/diagnostic/consts.go b/diagnostic/consts.go
index 6a7e4449..57db38c8 100644
--- a/diagnostic/consts.go
+++ b/diagnostic/consts.go
@@ -34,4 +34,5 @@ const (
 	cliConfigurationBaseName  = "cli-configuration.json"
 	configurationBaseName     = "configuration.json"
 	taskResultBaseName        = "task-result.json"
+	prechecksBaseName         = "prechecks.json"
 )
diff --git a/diagnostic/diagnostic.go b/diagnostic/diagnostic.go
index 92d760f6..5b29b591 100644
--- a/diagnostic/diagnostic.go
+++ b/diagnostic/diagnostic.go
@@ -6,6 +6,7 @@ import (
 	"errors"
 	"fmt"
 	"io"
+	"net"
 	"net/url"
 	"os"
 	"path/filepath"
@@ -16,6 +17,8 @@ import (
 	"github.com/rs/zerolog"
 
 	network "github.com/cloudflare/cloudflared/diagnostic/network"
+	"github.com/cloudflare/cloudflared/edgediscovery/allregions"
+	"github.com/cloudflare/cloudflared/prechecks"
 )
 
 const (
@@ -32,6 +35,7 @@ const (
 	networkInformationJobName    = "network information"
 	cliConfigurationJobName      = "cli configuration"
 	configurationJobName         = "configuration"
+	prechecksJobName             = "connectivity pre-checks"
 )
 
 // Struct used to hold the results of different routines executing the network collection.
@@ -92,6 +96,7 @@ type Options struct {
 	Address        string
 	ContainerID    string
 	PodID          string
+	Region         string
 	Toggles        Toggles
 }
 
@@ -230,7 +235,7 @@ func networkInformationCollectors() (rawNetworkCollector, jsonNetworkCollector c
 }
 
 func rawNetworkInformationWriter(resultMap map[string]networkCollectionResult) (string, error) {
-	// nolint: gosec
+	// nolint: gosec // Intentionally creating a temporary diagnostic file in the OS temp directory.
 	networkDumpHandle, err := os.Create(filepath.Join(os.TempDir(), rawNetworkBaseName))
 	if err != nil {
 		return "", ErrCreatingTemporaryFile
@@ -372,6 +377,7 @@ func resolveInstanceBaseURL(
 func createJobs(
 	client *httpClient,
 	tunnel *TunnelState,
+	region string,
 	diagContainer string,
 	diagPod string,
 	noDiagSystem bool,
@@ -434,11 +440,55 @@ func createJobs(
 			fn:      collectFromEndpointAdapter(client.GetTunnelConfiguration, configurationBaseName),
 			bypass:  false,
 		},
+		{
+			jobName: prechecksJobName,
+			fn:      collectPrechecks(region),
+			bypass:  noDiagNetwork,
+		},
 	}
 
 	return jobs
 }
 
+// collectPrechecks runs connectivity pre-checks and writes the results to a JSON file.
+func collectPrechecks(region string) collectFunc {
+	return func(ctx context.Context) (string, error) {
+		cfg := prechecks.Config{
+			Region:    region,
+			IPVersion: allregions.Auto,
+			Timeout:   defaultTimeout,
+		}
+
+		// Create a no-op logger since we don't want to spam logs during diagnostic collection
+		log := zerolog.New(io.Discard)
+
+		dialers := prechecks.RunDialers{
+			DNSResolver:      &prechecks.EdgeDNSResolver{Log: &log},
+			TCPDialer:        &prechecks.EdgeTCPDialer{},
+			QUICDialer:       &prechecks.EdgeQUICDialer{},
+			ManagementDialer: &prechecks.NetManagementDialer{Dialer: net.Dialer{}},
+		}
+
+		emptyCert := ""
+		report := prechecks.Run(ctx, emptyCert, cfg, &log, dialers)
+
+		// Write the report to a JSON file
+		// nolint: gosec
+		dumpHandle, err := os.Create(filepath.Join(os.TempDir(), prechecksBaseName))
+		if err != nil {
+			return "", ErrCreatingTemporaryFile
+		}
+		defer func() { _ = dumpHandle.Close() }()
+
+		encoder := newFormattedEncoder(dumpHandle)
+		if err := encoder.Encode(report); err != nil {
+			return dumpHandle.Name(), fmt.Errorf("error encoding prechecks report: %w", err)
+		}
+
+		return dumpHandle.Name(), nil
+	}
+}
+
 func createTaskReport(taskReport map[string]taskResult) (string, error) {
 	// nolint: gosec
 	dumpHandle, err := os.Create(filepath.Join(os.TempDir(), taskResultBaseName))
@@ -527,6 +577,7 @@ func RunDiagnostic(
 	jobs := createJobs(
 		client,
 		tunnel,
+		options.Region,
 		options.ContainerID,
 		options.PodID,
 		options.Toggles.NoDiagSystem,
diff --git a/supervisor/tunnel.go b/supervisor/tunnel.go
index 2a2f41c0..3641b19c 100644
--- a/supervisor/tunnel.go
+++ b/supervisor/tunnel.go
@@ -65,6 +65,9 @@ type TunnelConfig struct {
 	// NoPrechecks disables connectivity pre-checks at startup.
 	NoPrechecks bool
 
+	// Prechecks enables connectivity pre-checks at startup.
+	Prechecks bool
+
 	NamedTunnel         *connection.TunnelProperties
 	ProtocolSelector    connection.ProtocolSelector
 	EdgeTLSConfigs      map[connection.Protocol]*tls.Config