diff --git a/test/new-e2e/pkg/utils/e2e/client/agent_client.go b/test/new-e2e/pkg/utils/e2e/client/agent_client.go
index d2c7bb7d343e7..7a2999316181d 100644
--- a/test/new-e2e/pkg/utils/e2e/client/agent_client.go
+++ b/test/new-e2e/pkg/utils/e2e/client/agent_client.go
@@ -7,6 +7,8 @@ package client
 
 import (
 	"fmt"
+	"github.com/DataDog/datadog-agent/test/new-e2e/pkg/runner"
+	"regexp"
 	"strings"
 	"testing"
 	"time"
@@ -40,7 +42,7 @@ func NewHostAgentClient(context e2e.Context, hostOutput remote.HostOutput, waitF
 	commandRunner := newAgentCommandRunner(context.T(), ae)
 
 	if params.ShouldWaitForReady {
-		if err := commandRunner.waitForReadyTimeout(agentReadyTimeout); err != nil {
+		if err := waitForReadyTimeout(context.T(), host, commandRunner, agentReadyTimeout); err != nil {
 			return nil, err
 		}
 	}
@@ -61,7 +63,7 @@ func NewHostAgentClientWithParams(context e2e.Context, hostOutput remote.HostOut
 	commandRunner := newAgentCommandRunner(context.T(), ae)
 
 	if params.ShouldWaitForReady {
-		if err := commandRunner.waitForReadyTimeout(agentReadyTimeout); err != nil {
+		if err := waitForReadyTimeout(context.T(), host, commandRunner, agentReadyTimeout); err != nil {
 			return nil, err
 		}
 	}
@@ -127,7 +129,7 @@ func ensureAuthToken(params *agentclientparams.Params, _ osComp.Family, host *Ho
 	if err != nil {
 		return fmt.Errorf("could not read auth token file: %v", err)
 	}
-	params.AuthToken = strings.TrimSpace(string(authToken))
+	params.AuthToken = strings.TrimSpace(authToken)
 
 	return nil
 }
@@ -169,3 +171,97 @@ func curlCommand(endpoint string, authToken string) string {
 		endpoint,
 	)
 }
+
+func waitForReadyTimeout(t *testing.T, host *Host, commandRunner *agentCommandRunner, timeout time.Duration) error {
+	err := commandRunner.waitForReadyTimeout(timeout)
+
+	if err != nil {
+		// Propagate the original error if we have another error here
+		localErr := generateAndDownloadFlare(t, commandRunner, host)
+
+		if localErr != nil {
+			t.Errorf("Could not generate and get a flare: %v", localErr)
+		}
+	}
+
+	return err
+}
+
+func generateAndDownloadFlare(t *testing.T, commandRunner *agentCommandRunner, host *Host) error {
+	profile := runner.GetProfile()
+	outputDir, err := profile.GetOutputDir()
+	flareFound := false
+
+	if err != nil {
+		return fmt.Errorf("could not get output directory: %v", err)
+	}
+
+	_, err = commandRunner.FlareWithError(agentclient.WithArgs([]string{"--email", "e2e@test.com", "--send", "--local"}))
+	if err != nil {
+		t.Errorf("Error while generating the flare: %v.", err)
+		// Do not return now, the flare may be generated locally but was not uploaded because there's no fake intake
+	}
+
+	flareRegex, err := regexp.Compile(`datadog-agent-.*\.zip`)
+	if err != nil {
+		return fmt.Errorf("could not compile regex: %v", err)
+	}
+
+	tmpFolder, err := host.GetTmpFolder()
+	if err != nil {
+		return fmt.Errorf("could not get tmp folder: %v", err)
+	}
+
+	entries, err := host.ReadDir(tmpFolder)
+	if err != nil {
+		return fmt.Errorf("could not read directory: %v", err)
+	}
+
+	for _, entry := range entries {
+		if flareRegex.MatchString(entry.Name()) {
+			t.Logf("Found flare file: %s", entry.Name())
+
+			if host.osFamily != osComp.WindowsFamily {
+				_, err = host.Execute(fmt.Sprintf("sudo chmod 744 %s/%s", tmpFolder, entry.Name()))
+				if err != nil {
+					return fmt.Errorf("could not update permission of flare file %s/%s : %v", tmpFolder, entry.Name(), err)
+				}
+			}
+
+			t.Logf("Downloading flare file in: %s", outputDir)
+			err = host.GetFile(fmt.Sprintf("%s/%s", tmpFolder, entry.Name()), fmt.Sprintf("%s/%s", outputDir, entry.Name()))
+
+			if err != nil {
+				return fmt.Errorf("could not download flare file from %s/%s : %v", tmpFolder, entry.Name(), err)
+			}
+
+			flareFound = true
+		}
+	}
+
+	if !flareFound {
+		t.Errorf("Could not find a flare. Retrieving logs directly instead...")
+
+		logsFolder, err := host.GetLogsFolder()
+		if err != nil {
+			return fmt.Errorf("could not get logs folder: %v", err)
+		}
+
+		entries, err = host.ReadDir(logsFolder)
+
+		if err != nil {
+			return fmt.Errorf("could not read directory: %v", err)
+		}
+
+		for _, entry := range entries {
+			t.Logf("Found log file: %s. Downloading file in: %s", entry.Name(), outputDir)
+
+			err = host.GetFile(fmt.Sprintf("%s/%s", logsFolder, entry.Name()), fmt.Sprintf("%s/%s", outputDir, entry.Name()))
+			if err != nil {
+				return fmt.Errorf("could not download log file from %s/%s : %v", logsFolder, entry.Name(), err)
+			}
+		}
+	}
+
+	return nil
+}
diff --git a/test/new-e2e/pkg/utils/e2e/client/agent_commands.go b/test/new-e2e/pkg/utils/e2e/client/agent_commands.go
index c0536aabd9a3d..2aabdc98373ed 100644
--- a/test/new-e2e/pkg/utils/e2e/client/agent_commands.go
+++ b/test/new-e2e/pkg/utils/e2e/client/agent_commands.go
@@ -112,6 +112,15 @@ func (agent *agentCommandRunner) Flare(commandArgs ...agentclient.AgentArgsOptio
 	return agent.executeCommand("flare", commandArgs...)
 }
 
+// FlareWithError runs flare command and returns the output or an error. You should use the FakeIntake client to fetch the flare archive
+func (agent *agentCommandRunner) FlareWithError(commandArgs ...agentclient.AgentArgsOption) (string, error) {
+	args, err := optional.MakeParams(commandArgs...)
+	require.NoError(agent.t, err)
+
+	arguments := append([]string{"flare"}, args.Args...)
+	return agent.executor.execute(arguments)
+}
+
 // Health runs health command and returns the runtime agent health
 func (agent *agentCommandRunner) Health() (string, error) {
 	arguments := []string{"health"}
diff --git a/test/new-e2e/pkg/utils/e2e/client/host.go b/test/new-e2e/pkg/utils/e2e/client/host.go
index 67d554f6e5c05..ea76cb6b513e3 100644
--- a/test/new-e2e/pkg/utils/e2e/client/host.go
+++ b/test/new-e2e/pkg/utils/e2e/client/host.go
@@ -51,6 +51,7 @@ type Host struct {
 	privateKeyPassphrase []byte
 	buildCommand         buildCommandFn
 	convertPathSeparator convertPathSeparatorFn
+	osFamily             oscomp.Family
 }
 
 // NewHost creates a new ssh client to connect to a remote host with
@@ -82,6 +83,7 @@ func NewHost(context e2e.Context, hostOutput remote.HostOutput) (*Host, error) {
 		privateKeyPassphrase: []byte(privateKeyPassword),
 		buildCommand:         buildCommandFactory(hostOutput.OSFamily),
 		convertPathSeparator: convertPathSeparatorFactory(hostOutput.OSFamily),
+		osFamily:             hostOutput.OSFamily,
 	}
 	err = host.Reconnect()
 	return host, err
@@ -316,6 +318,32 @@ func (h *Host) DialPort(port uint16) (net.Conn, error) {
 	return connection, err
 }
 
+// GetTmpFolder returns the temporary folder path for the host
+func (h *Host) GetTmpFolder() (string, error) {
+	switch osFamily := h.osFamily; osFamily {
+	case oscomp.WindowsFamily:
+		return h.Execute("echo %TEMP%")
+	case oscomp.LinuxFamily:
+		return "/tmp", nil
+	default:
+		return "", errors.ErrUnsupported
+	}
+}
+
+// GetLogsFolder returns the logs folder path for the host
+func (h *Host) GetLogsFolder() (string, error) {
+	switch osFamily := h.osFamily; osFamily {
+	case oscomp.WindowsFamily:
+		return `C:\ProgramData\Datadog\logs`, nil
+	case oscomp.LinuxFamily:
+		return "/var/log/datadog/", nil
+	case oscomp.MacOSFamily:
+		return "/opt/datadog-agent/logs", nil
+	default:
+		return "", errors.ErrUnsupported
+	}
+}
+
 // appendWithSudo appends content to the file using sudo tee for Linux environment
 func (h *Host) appendWithSudo(path string, content []byte) (int64, error) {
 	cmd := fmt.Sprintf("echo '%s' | sudo tee -a %s", string(content), path)