package service

import (
	"context"
	"database/sql"
	"encoding/json"
	"errors"
	"fmt"
	"log/slog"
	"net/http"
	"net/url"

	"github.com/fleetdm/fleet/v4/ee/server/service/hostidentity/httpsig"
	"github.com/fleetdm/fleet/v4/server"
	"github.com/fleetdm/fleet/v4/server/contexts/capabilities"
	"github.com/fleetdm/fleet/v4/server/contexts/ctxdb"
	"github.com/fleetdm/fleet/v4/server/contexts/ctxerr"
	hostctx "github.com/fleetdm/fleet/v4/server/contexts/host"
	"github.com/fleetdm/fleet/v4/server/contexts/license"
	"github.com/fleetdm/fleet/v4/server/contexts/logging"
	"github.com/fleetdm/fleet/v4/server/fleet"
	"github.com/fleetdm/fleet/v4/server/mdm"
	microsoft_mdm "github.com/fleetdm/fleet/v4/server/mdm/microsoft"
	"github.com/fleetdm/fleet/v4/server/ptr"
	"github.com/fleetdm/fleet/v4/server/service/osquery_utils"
	"github.com/fleetdm/fleet/v4/server/worker"
)

// enrollOrbitResponse wraps the fleet type to add HijackRender.
type enrollOrbitResponse struct {
	fleet.EnrollOrbitResponse
}

// HijackRender so we can add a header with the server capabilities in the
// response, allowing Orbit to know what features are available without the
// need to enroll.
func (r enrollOrbitResponse) HijackRender(ctx context.Context, w http.ResponseWriter) {
	writeCapabilitiesHeader(w, fleet.GetServerOrbitCapabilities())
	enc := json.NewEncoder(w)
	enc.SetIndent("", "  ")

	if err := enc.Encode(r); err != nil {
		encodeError(ctx, newOsqueryError(fmt.Sprintf("orbit enroll failed: %s", err)), w)
	}
}

func enrollOrbitEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.EnrollOrbitRequest)
	nodeKey, err := svc.EnrollOrbit(ctx, fleet.OrbitHostInfo{
		HardwareUUID:      req.HardwareUUID,
		HardwareSerial:    req.HardwareSerial,
		Hostname:          req.Hostname,
		Platform:          req.Platform,
		PlatformLike:      req.PlatformLike,
		OsqueryIdentifier: req.OsqueryIdentifier,
		ComputerName:      req.ComputerName,
		HardwareModel:     req.HardwareModel,
	}, req.EnrollSecret, req.EUAToken)
	if err != nil {
		return enrollOrbitResponse{fleet.EnrollOrbitResponse{Err: err}}, nil
	}
	return enrollOrbitResponse{fleet.EnrollOrbitResponse{OrbitNodeKey: nodeKey}}, nil
}

func (svc *Service) AuthenticateOrbitHost(ctx context.Context, orbitNodeKey string) (*fleet.Host, bool, error) {
	svc.authz.SkipAuthorization(ctx)

	if orbitNodeKey == "" {
		return nil, false, ctxerr.Wrap(ctx, fleet.NewAuthRequiredError("authentication error: missing orbit node key"))
	}

	host, err := svc.ds.LoadHostByOrbitNodeKey(ctx, orbitNodeKey)
	switch {
	case err == nil:
		// OK
	case fleet.IsNotFound(err):
		return nil, false, ctxerr.Wrap(ctx, fleet.NewAuthRequiredError("authentication error: invalid orbit node key"))
	default:
		return nil, false, ctxerr.Wrap(ctx, err, "authentication error orbit")
	}

	if *host.HasHostIdentityCert {
		err = httpsig.VerifyHostIdentity(ctx, svc.ds, host)
		if err != nil {
			return nil, false, ctxerr.Wrap(ctx, fleet.NewAuthRequiredError(fmt.Sprintf("authentication error orbit: %s", err.Error())))
		}
	}

	return host, svc.debugEnabledForHost(ctx, host.ID), nil
}

// processWindowsEUAToken validates a Fleet-signed EUA token from the Windows MSI
// installer, links the user's IdP account to the host, and returns the UPN and
// device ID for use in post-enrollment steps.
func (svc *Service) processWindowsEUAToken(ctx context.Context, hostUUID string, euaToken string) (upn string, deviceID string, err error) {
	if svc.wstepCertManager == nil {
		// Windows MDM is not configured on this server so the token cannot be validated.
		// Fall back to prompting the user for authentication.
		return "", "", fleet.NewOrbitIDPAuthRequiredError()
	}

	claims, tokenErr := svc.wstepCertManager.GetEUATokenClaims(euaToken)
	if tokenErr != nil {
		svc.logger.WarnContext(ctx, "EUA token validation failed, falling back to end user auth prompt",
			"err", tokenErr, "host_uuid", hostUUID)
		return "", "", fleet.NewOrbitIDPAuthRequiredError()
	}
	upn = claims.UPN
	deviceID = claims.DeviceID

	_, err = svc.ds.MDMWindowsGetEnrolledDeviceWithDeviceID(ctx, deviceID)
	if err != nil {
		if fleet.IsNotFound(err) {
			svc.logger.WarnContext(ctx, "EUA token device_id not found in windows mdm enrollments, falling back to end user auth prompt",
				"device_id", deviceID, "host_uuid", hostUUID)
			return "", "", fleet.NewOrbitIDPAuthRequiredError()
		}
		return "", "", ctxerr.Wrap(ctx, err, "getting windows mdm enrollment for EUA token")
	}

	// Fetch or create the mdm_idp_accounts row for this email.
	// Fetch first so we do not overwrite existing first/last names
	// that may have been populated by SCIM provisioning.
	acct, err := svc.ds.GetMDMIdPAccountByEmail(ctx, upn)
	if err != nil && !fleet.IsNotFound(err) {
		return "", "", ctxerr.Wrap(ctx, err, "getting mdm idp account by email for EUA token")
	}
	if fleet.IsNotFound(err) {
		if err := svc.ds.InsertMDMIdPAccount(ctx, &fleet.MDMIdPAccount{Email: upn, Username: upn}); err != nil {
			return "", "", ctxerr.Wrap(ctx, err, "inserting mdm idp account for EUA token")
		}
		// Re-fetch to get the UUID assigned by the DB.
		acct, err = svc.ds.GetMDMIdPAccountByEmail(ctxdb.RequirePrimary(ctx, true), upn)
		if err != nil {
			return "", "", ctxerr.Wrap(ctx, err, "re-fetching mdm idp account after insert for EUA token")
		}
	}
	if acct == nil {
		return "", "", ctxerr.New(ctx, "mdm idp account not found for EUA token")
	}

	// Link the IdP account to this host UUID in host_mdm_idp_accounts.
	if err := svc.ds.AssociateHostMDMIdPAccountDB(ctx, hostUUID, acct.UUID); err != nil {
		return "", "", ctxerr.Wrap(ctx, err, "associating host with mdm idp account for EUA token")
	}

	return upn, deviceID, nil
}

// EnrollOrbit enrolls an Orbit instance to Fleet and returns the orbit node key.
func (svc *Service) EnrollOrbit(ctx context.Context, hostInfo fleet.OrbitHostInfo, enrollSecret string, euaToken string) (string, error) {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	logging.WithLevel(
		logging.WithExtras(ctx,
			"hardware_uuid", hostInfo.HardwareUUID,
			"hardware_serial", hostInfo.HardwareSerial,
			"hostname", hostInfo.Hostname,
			"platform", hostInfo.Platform,
			"platform_like", hostInfo.PlatformLike,
			"osquery_identifier", hostInfo.OsqueryIdentifier,
			"computer_name", hostInfo.ComputerName,
			"hardware_model", hostInfo.HardwareModel,
		),
		slog.LevelInfo,
	)

	secret, err := svc.ds.VerifyEnrollSecret(ctx, enrollSecret)
	if err != nil {
		if fleet.IsNotFound(err) {
			// OK - This can happen if the following sequence of events take place:
			// 	1. User deletes global/team enroll secret.
			// 	2. User deletes the host in Fleet.
			// 	3. Orbit tries to re-enroll using old secret.
			return "", fleet.NewAuthFailedError("invalid secret")
		}
		return "", fleet.OrbitError{Message: err.Error()}
	}

	identifier := hostInfo.OsqueryIdentifier
	if identifier == "" {
		identifier = hostInfo.HardwareUUID
	}

	identityCert, err := svc.ds.GetHostIdentityCertByName(ctx, identifier)
	if err != nil && !fleet.IsNotFound(err) {
		return "", fleet.OrbitError{Message: fmt.Sprintf("loading certificate: %s", err.Error())}
	}

	// If an identity certificate exists for this host, make sure the request had an HTTP message signature with the matching certificate.
	hostIdentityCert, httpSigPresent := httpsig.FromContext(ctx)
	if identityCert != nil {
		if !httpSigPresent {
			return "", fleet.NewAuthFailedError("authentication error: missing HTTP signature")
		}
		if identityCert.SerialNumber != hostIdentityCert.SerialNumber {
			return "", fleet.NewAuthFailedError("authentication error: certificate serial number mismatch")
		}
	} else if httpSigPresent { // but we couldn't find the cert in DB
		return "", fleet.NewAuthFailedError("authentication error: certificate matching HTTP message signature not found")
	}

	orbitNodeKey, err := server.GenerateRandomText(svc.config.Osquery.NodeKeySize)
	if err != nil {
		return "", fleet.OrbitError{Message: "failed to generate orbit node key: " + err.Error()}
	}

	appConfig, err := svc.ds.AppConfig(ctx)
	if err != nil {
		return "", fleet.OrbitError{Message: "app config load failed: " + err.Error()}
	}
	isEndUserAuthRequired := appConfig.MDM.MacOSSetup.EnableEndUserAuthentication
	// If the secret is for a team, get the team config as well.
	if secret.TeamID != nil {
		team, err := svc.ds.TeamLite(ctx, *secret.TeamID)
		if err != nil {
			return "", fleet.OrbitError{Message: "failed to get team config: " + err.Error()}
		}
		isEndUserAuthRequired = team.Config.MDM.MacOSSetup.EnableEndUserAuthentication
	}

	var euaDeviceID, euaUPN string

	if isEndUserAuthRequired {
		if hostInfo.HardwareUUID == "" {
			return "", fleet.OrbitError{Message: "failed to get IdP account: hardware uuid is empty"}
		}
		// Try to find an IdP account for this host.
		idpAccount, err := svc.ds.GetMDMIdPAccountByHostUUID(ctx, hostInfo.HardwareUUID)
		if err != nil {
			return "", fleet.OrbitError{Message: "failed to get IdP account: " + err.Error()}
		}
		if idpAccount == nil {
			// Get the host platform.
			h := fleet.Host{
				Platform:     hostInfo.Platform,
				PlatformLike: hostInfo.PlatformLike,
			}
			platform := h.FleetPlatform()
			// Orbit enrollment is only gated by end user auth for Linux and Windows hosts.
			// For macOS hosts the MDM enrollment process handles end user auth.
			if platform == "linux" || platform == "windows" {
				// If the Orbit client doesn't support end user auth, complain loudly and let the host enroll.
				mp, ok := capabilities.FromContext(ctx)
				switch {
				case !ok:
					svc.logger.ErrorContext(ctx, "allowing unauthenticated enrollment: could not determine orbit end-user auth capability", "host_uuid", hostInfo.HardwareUUID)
				case !mp.Has(fleet.CapabilityEndUserAuth):
					svc.logger.WarnContext(ctx, "allowing unauthenticated enrollment: orbit version does not support end-user authentication", "host_uuid", hostInfo.HardwareUUID)
				case platform == "windows" && euaToken != "":
					// A Windows host already authenticated during MDM enrollment and the
					// EUA token was passed by the MSI installer.
					upn, deviceID, err := svc.processWindowsEUAToken(ctx, hostInfo.HardwareUUID, euaToken)
					if err != nil {
						return "", err
					}
					euaUPN = upn
					euaDeviceID = deviceID
					// Continue enrollment — do not return END_USER_AUTH_REQUIRED.
				default:
					// Otherwise report the unauthenticated host and let Orbit handle it (e.g. by prompting the user to authenticate).
					return "", fleet.NewOrbitIDPAuthRequiredError()
				}
			}
		}
	}

	var stickyEnrollment *string
	if svc.keyValueStore != nil {
		// Check for sticky MDM enrollment flag. When set (e.g., after a host transfer),
		// this prevents enrollment-based team changes for a time window to avoid race conditions
		// with MDM profile delivery.
		stickyEnrollment, err = svc.keyValueStore.Get(ctx, fleet.StickyMDMEnrollmentKeyPrefix+hostInfo.HardwareUUID)
		if err != nil {
			// Log error but continue enrollment (fail-open approach). If Redis is unavailable,
			// enrollment proceeds without sticky behavior rather than blocking.
			svc.logger.ErrorContext(ctx, "failed to get sticky enrollment", "err", err, "host_uuid", hostInfo.HardwareUUID)
		}
	}

	host, err := svc.ds.EnrollOrbit(ctx,
		fleet.WithEnrollOrbitMDMEnabled(appConfig.MDM.EnabledAndConfigured),
		fleet.WithEnrollOrbitHostInfo(hostInfo),
		fleet.WithEnrollOrbitNodeKey(orbitNodeKey),
		fleet.WithEnrollOrbitTeamID(secret.TeamID),
		fleet.WithEnrollOrbitIdentityCert(identityCert),
		fleet.WithEnrollOrbitIgnoreTeamUpdate(stickyEnrollment != nil),
	)
	if err != nil {
		return "", fleet.OrbitError{Message: "failed to enroll " + err.Error()}
	}

	if euaDeviceID != "" {
		updated, err := svc.ds.UpdateMDMWindowsEnrollmentsHostUUID(ctx, host.UUID, euaDeviceID)
		if err != nil {
			svc.logger.ErrorContext(ctx, "failed to link windows mdm enrollment to orbit host via EUA token",
				"err", err, "host_uuid", host.UUID, "device_id", euaDeviceID)
		}

		if updated {
			scimUser, err := svc.ds.ScimUserByUserNameOrEmail(ctx, euaUPN, euaUPN)
			//nolint:gocritic // ignore ifElseChain
			if err != nil && !fleet.IsNotFound(err) && err != sql.ErrNoRows {
				svc.logger.ErrorContext(ctx, "failed to find SCIM user for EUA token enrollment",
					"err", err, "host_id", host.ID)
			} else if err == nil && scimUser != nil {
				if err := svc.ds.SetOrUpdateHostSCIMUserMapping(ctx, host.ID, scimUser.ID); err != nil {
					svc.logger.ErrorContext(ctx, "failed to set SCIM user mapping for EUA token enrollment",
						"err", err, "host_id", host.ID)
				}
			} else {
				if err := svc.ds.DeleteHostSCIMUserMapping(ctx, host.ID); err != nil && !fleet.IsNotFound(err) {
					svc.logger.ErrorContext(ctx, "failed to delete SCIM user mapping for EUA token enrollment",
						"err", err, "host_id", host.ID)
				}
			}
		}
	}

	// Associate the newly-enrolled host with a SCIM user if applicable.
	// Do this only for linux and windows devices, as macOS devices
	// are associated during MDM enrollment.
	platform := host.FleetPlatform()
	if platform == "linux" || platform == "windows" {
		svc.logger.DebugContext(ctx, "attempting to associate enrolled host with SCIM user", "host_id", host.ID, "platform", platform)
		if err := svc.ds.MaybeAssociateHostWithScimUser(ctx, host.ID); err != nil {
			svc.logger.ErrorContext(ctx, "failed to associate enrolled host with SCIM user", "err", err, "host_id", host.ID)
		}
	}

	if err := svc.NewActivity(
		ctx,
		nil,
		fleet.ActivityTypeFleetEnrolled{
			HostID:          host.ID,
			HostSerial:      hostInfo.HardwareSerial,
			HostDisplayName: host.DisplayName(),
		},
	); err != nil {
		svc.logger.ErrorContext(ctx, "record fleet enroll activity", "err", err)
	}

	return orbitNodeKey, nil
}

func getOrbitConfigEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	cfg, err := svc.GetOrbitConfig(ctx)
	if err != nil {
		return fleet.OrbitGetConfigResponse{Err: err}, nil
	}
	return fleet.OrbitGetConfigResponse{OrbitConfig: cfg}, nil
}

func (svc *Service) GetOrbitConfig(ctx context.Context) (fleet.OrbitConfig, error) {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		return fleet.OrbitConfig{}, fleet.OrbitError{Message: "internal error: missing host from request context"}
	}

	appConfig, err := svc.ds.AppConfig(ctx)
	if err != nil {
		return fleet.OrbitConfig{}, err
	}

	isConnectedToFleetMDM, err := svc.ds.IsHostConnectedToFleetMDM(ctx, host)
	if err != nil {
		return fleet.OrbitConfig{}, ctxerr.Wrap(ctx, err, "checking if host is connected to Fleet")
	}

	mdmInfo, err := svc.ds.GetHostMDM(ctx, host.ID)
	if err != nil && !errors.Is(err, sql.ErrNoRows) {
		return fleet.OrbitConfig{}, ctxerr.Wrap(ctx, err, "retrieving host mdm info")
	}

	// set the host's orbit notifications for macOS MDM
	var notifs fleet.OrbitConfigNotifications
	if appConfig.MDM.EnabledAndConfigured && host.IsOsqueryEnrolled() && host.Platform == "darwin" {
		needsDEPEnrollment := mdmInfo != nil && !mdmInfo.Enrolled && host.IsDEPAssignedToFleet()

		if needsDEPEnrollment {
			notifs.RenewEnrollmentProfile = true
		}

		manualMigrationEligible, err := fleet.IsEligibleForManualMigration(host, mdmInfo, isConnectedToFleetMDM)
		if err != nil {
			return fleet.OrbitConfig{}, ctxerr.Wrap(ctx, err, "checking manual migration eligibility")
		}

		if appConfig.MDM.MacOSMigration.Enable &&
			(fleet.IsEligibleForDEPMigration(host, mdmInfo, isConnectedToFleetMDM) || manualMigrationEligible) {
			notifs.NeedsMDMMigration = true
		}

		if isConnectedToFleetMDM {
			// If there is no software or script configured for setup experience and this is the
			// first time orbit is calling the /config endpoint, then this host
			// will not have a row in host_mdm_apple_awaiting_configuration.
			// On subsequent calls to /config, the host WILL have a row in
			// host_mdm_apple_awaiting_configuration.
			inSetupAssistant, err := svc.ds.GetHostAwaitingConfiguration(ctx, host.UUID)
			if err != nil && !fleet.IsNotFound(err) {
				return fleet.OrbitConfig{}, ctxerr.Wrap(ctx, err, "checking if host is in setup experience")
			}

			if inSetupAssistant {
				notifs.RunSetupExperience = true
			}

			if inSetupAssistant {
				// If the client is running a fleetd that doesn't support setup
				// experience, then we should fall back to the "old way" of releasing
				// the device.
				mp, ok := capabilities.FromContext(ctx)
				if !ok || !mp.Has(fleet.CapabilitySetupExperience) {
					svc.logger.DebugContext(ctx, "host doesn't support setup experience, falling back to worker-based device release", "host_uuid", host.UUID)
					if err := svc.processReleaseDeviceForOldFleetd(ctx, host); err != nil {
						return fleet.OrbitConfig{}, err
					}
				}
			}
		}
	}

	// set the host's orbit notifications for Windows MDM
	if appConfig.MDM.WindowsEnabledAndConfigured && !appConfig.MDM.EnableTurnOnWindowsMDMManually {
		if isEligibleForWindowsMDMEnrollment(host, mdmInfo) {
			discoURL, err := microsoft_mdm.ResolveWindowsMDMDiscovery(appConfig.ServerSettings.ServerURL)
			if err != nil {
				return fleet.OrbitConfig{}, err
			}
			notifs.WindowsMDMDiscoveryEndpoint = discoURL
			notifs.NeedsProgrammaticWindowsMDMEnrollment = true
		} else if appConfig.MDM.WindowsMigrationEnabled && isEligibleForWindowsMDMMigration(host, mdmInfo) {
			notifs.NeedsMDMMigration = true

			// Set the host to refetch the "critical queries" quickly for some time,
			// to improve ingestion time of the unenroll and make the host eligible to
			// enroll into Fleet faster.
			if host.RefetchCriticalQueriesUntil == nil {
				refetchUntil := svc.clock.Now().Add(fleet.RefetchMDMUnenrollCriticalQueryDuration)
				host.RefetchCriticalQueriesUntil = &refetchUntil
				if err := svc.ds.UpdateHostRefetchCriticalQueriesUntil(ctx, host.ID, &refetchUntil); err != nil {
					return fleet.OrbitConfig{}, err
				}
			}
		}
	}
	if !appConfig.MDM.WindowsEnabledAndConfigured {
		if host.IsEligibleForWindowsMDMUnenrollment(isConnectedToFleetMDM) {
			notifs.NeedsProgrammaticWindowsMDMUnenrollment = true
		}
	}

	// load the (active, ready to execute) pending script executions for that host
	pending, err := svc.ds.ListReadyToExecuteScriptsForHost(ctx, host.ID, appConfig.ServerSettings.ScriptsDisabled)
	if err != nil {
		return fleet.OrbitConfig{}, err
	}
	if len(pending) > 0 {
		execIDs := make([]string, 0, len(pending))
		for _, p := range pending {
			execIDs = append(execIDs, p.ExecutionID)
		}
		notifs.PendingScriptExecutionIDs = execIDs
	}

	notifs.RunDiskEncryptionEscrow = host.IsLUKSSupported() &&
		host.DiskEncryptionEnabled != nil &&
		*host.DiskEncryptionEnabled &&
		svc.ds.IsHostPendingEscrow(ctx, host.ID)

	// load the (active, ready to execute) pending software install executions for that host
	pendingInstalls, err := svc.ds.ListReadyToExecuteSoftwareInstalls(ctx, host.ID)
	if err != nil {
		return fleet.OrbitConfig{}, err
	}
	if len(pendingInstalls) > 0 {
		notifs.PendingSoftwareInstallerIDs = pendingInstalls
	}

	// team ID is not nil, get team specific flags and options
	if host.TeamID != nil {
		teamAgentOptions, err := svc.ds.TeamAgentOptions(ctx, *host.TeamID)
		if err != nil {
			return fleet.OrbitConfig{}, err
		}

		var opts fleet.AgentOptions
		if teamAgentOptions != nil && len(*teamAgentOptions) > 0 {
			if err := json.Unmarshal(*teamAgentOptions, &opts); err != nil {
				return fleet.OrbitConfig{}, err
			}
		}

		// Fall back to the global app config's script execution timeout when the
		// team has no explicit override. Other agent-options fields are intentionally
		// not inherited from the global config.
		if opts.ScriptExecutionTimeout == 0 && appConfig.AgentOptions != nil {
			var globalOpts fleet.AgentOptions
			if err := json.Unmarshal(*appConfig.AgentOptions, &globalOpts); err != nil {
				return fleet.OrbitConfig{}, ctxerr.Wrap(ctx, err, "unmarshal global agent options for script timeout fallback")
			}
			opts.ScriptExecutionTimeout = globalOpts.ScriptExecutionTimeout
		}

		extensionsFiltered, err := svc.filterExtensionsForHost(ctx, opts.Extensions, host)
		if err != nil {
			return fleet.OrbitConfig{}, err
		}

		mdmConfig, err := svc.ds.TeamMDMConfig(ctx, *host.TeamID)
		if err != nil {
			return fleet.OrbitConfig{}, err
		}

		var nudgeConfig *fleet.NudgeConfig
		if appConfig.MDM.EnabledAndConfigured &&
			mdmConfig != nil &&
			host.IsOsqueryEnrolled() &&
			isConnectedToFleetMDM &&
			mdmConfig.MacOSUpdates.Configured() {

			hostOS, err := svc.ds.GetHostOperatingSystem(ctx, host.ID)
			if errors.Is(err, sql.ErrNoRows) {
				// host os has not been collected yet (no details query)
				hostOS = &fleet.OperatingSystem{}
			} else if err != nil {
				return fleet.OrbitConfig{}, err
			}
			requiresNudge, err := hostOS.RequiresNudge()
			if err != nil {
				return fleet.OrbitConfig{}, err
			}

			if requiresNudge {
				nudgeConfig, err = fleet.NewNudgeConfig(mdmConfig.MacOSUpdates)
				if err != nil {
					return fleet.OrbitConfig{}, err
				}
			}
		}

		err = svc.setDiskEncryptionNotifications(
			ctx,
			&notifs,
			host,
			appConfig,
			mdmConfig.EnableDiskEncryption,
			isConnectedToFleetMDM,
			mdmInfo,
		)
		if err != nil {
			return fleet.OrbitConfig{}, ctxerr.Wrap(ctx, err, "setting team disk encryption notifications")
		}

		var updateChannels *fleet.OrbitUpdateChannels
		if len(opts.UpdateChannels) > 0 {
			var uc fleet.OrbitUpdateChannels
			if err := json.Unmarshal(opts.UpdateChannels, &uc); err != nil {
				return fleet.OrbitConfig{}, err
			}
			updateChannels = &uc
		}

		// only unset this flag once we know there were no errors so this notification will be picked up by the agent
		if notifs.RunDiskEncryptionEscrow {
			_ = svc.ds.ClearPendingEscrow(ctx, host.ID)
		}

		return fleet.OrbitConfig{
			ScriptExeTimeout: opts.ScriptExecutionTimeout,
			Flags:            opts.CommandLineStartUpFlags,
			Extensions:       extensionsFiltered,
			Notifications:    notifs,
			NudgeConfig:      nudgeConfig,
			UpdateChannels:   updateChannels,
		}, nil
	}

	// team ID is nil, get global flags and options
	var opts fleet.AgentOptions
	if appConfig.AgentOptions != nil {
		if err := json.Unmarshal(*appConfig.AgentOptions, &opts); err != nil {
			return fleet.OrbitConfig{}, err
		}
	}

	extensionsFiltered, err := svc.filterExtensionsForHost(ctx, opts.Extensions, host)
	if err != nil {
		return fleet.OrbitConfig{}, err
	}

	var nudgeConfig *fleet.NudgeConfig
	if appConfig.MDM.EnabledAndConfigured &&
		isConnectedToFleetMDM &&
		host.IsOsqueryEnrolled() &&
		appConfig.MDM.MacOSUpdates.Configured() {
		hostOS, err := svc.ds.GetHostOperatingSystem(ctx, host.ID)
		if errors.Is(err, sql.ErrNoRows) {
			// host os has not been collected yet (no details query)
			hostOS = &fleet.OperatingSystem{}
		} else if err != nil {
			return fleet.OrbitConfig{}, err
		}
		requiresNudge, err := hostOS.RequiresNudge()
		if err != nil {
			return fleet.OrbitConfig{}, err
		}

		if requiresNudge {
			nudgeConfig, err = fleet.NewNudgeConfig(appConfig.MDM.MacOSUpdates)
			if err != nil {
				return fleet.OrbitConfig{}, err
			}
		}
	}

	err = svc.setDiskEncryptionNotifications(
		ctx,
		&notifs,
		host,
		appConfig,
		appConfig.MDM.EnableDiskEncryption.Value,
		isConnectedToFleetMDM,
		mdmInfo,
	)
	if err != nil {
		return fleet.OrbitConfig{}, ctxerr.Wrap(ctx, err, "setting no-team disk encryption notifications")
	}

	var updateChannels *fleet.OrbitUpdateChannels
	if len(opts.UpdateChannels) > 0 {
		var uc fleet.OrbitUpdateChannels
		if err := json.Unmarshal(opts.UpdateChannels, &uc); err != nil {
			return fleet.OrbitConfig{}, err
		}
		updateChannels = &uc
	}

	// only unset this flag once we know there were no errors so this notification will be picked up by the agent
	if notifs.RunDiskEncryptionEscrow {
		_ = svc.ds.ClearPendingEscrow(ctx, host.ID)
	}

	return fleet.OrbitConfig{
		ScriptExeTimeout: opts.ScriptExecutionTimeout,
		Flags:            opts.CommandLineStartUpFlags,
		Extensions:       extensionsFiltered,
		Notifications:    notifs,
		NudgeConfig:      nudgeConfig,
		UpdateChannels:   updateChannels,
	}, nil
}

func (svc *Service) processReleaseDeviceForOldFleetd(ctx context.Context, host *fleet.Host) error {
	var manualRelease bool
	if host.TeamID == nil {
		ac, err := svc.ds.AppConfig(ctx)
		if err != nil {
			return ctxerr.Wrap(ctx, err, "get AppConfig to read apple_enable_release_device_manually")
		}
		manualRelease = ac.MDM.MacOSSetup.EnableReleaseDeviceManually.Value
	} else {
		tm, err := svc.ds.TeamLite(ctx, *host.TeamID)
		if err != nil {
			return ctxerr.Wrap(ctx, err, "get Team to read apple_enable_release_device_manually")
		}
		manualRelease = tm.Config.MDM.MacOSSetup.EnableReleaseDeviceManually.Value
	}

	if !manualRelease {
		// For the commands to await, since we're in an orbit endpoint we know that
		// fleetd has already been installed, so we only need to check for the
		// bootstrap package install and the SSO account configuration (both are
		// optional).
		bootstrapCmdUUID, err := svc.ds.GetHostBootstrapPackageCommand(ctx, host.UUID)
		if err != nil && !fleet.IsNotFound(err) {
			return ctxerr.Wrap(ctx, err, "get bootstrap package command")
		}

		// AccountConfiguration covers the (optional) command to setup SSO.
		adminTeamFilter := fleet.TeamFilter{
			User: &fleet.User{GlobalRole: ptr.String(fleet.RoleAdmin)},
		}
		acctCmds, _, _, err := svc.ds.ListMDMCommands(ctx, adminTeamFilter, &fleet.MDMCommandListOptions{
			// PerPage 1: only acctCmds[0] is read below.
			ListOptions: fleet.ListOptions{PerPage: 1},
			Filters: fleet.MDMCommandFilters{
				HostIdentifier: host.UUID,
				RequestType:    "AccountConfiguration",
			},
		})
		if err != nil {
			return ctxerr.Wrap(ctx, err, "list AccountConfiguration commands")
		}
		var acctConfigCmdUUID string
		if len(acctCmds) > 0 {
			// there may be more than one if e.g. the worker job that sends them had to
			// retry, but they would all be processed anyway so we can only care about
			// the first one.
			acctConfigCmdUUID = acctCmds[0].CommandUUID
		}

		// Enroll reference arg is not used in the release device task, passing empty string.
		if err := worker.QueueAppleMDMJob(ctx, svc.ds, svc.logger, worker.AppleMDMPostDEPReleaseDeviceTask,
			host.UUID, host.Platform, host.TeamID, "", false, false, bootstrapCmdUUID, acctConfigCmdUUID); err != nil {
			return ctxerr.Wrap(ctx, err, "queue Apple Post-DEP release device job")
		}
	}

	// at this point we know for sure that it will get released, but we need to
	// ensure we won't continually enqueue new worker jobs for that host until it
	// is released. To do so, we clear up the setup experience data (since anyway
	// this host will not go through that new flow).
	if err := svc.ds.SetHostAwaitingConfiguration(ctx, host.UUID, false); err != nil {
		return ctxerr.Wrap(ctx, err, "unset host awaiting configuration")
	}

	return nil
}

func (svc *Service) setDiskEncryptionNotifications(
	ctx context.Context,
	notifs *fleet.OrbitConfigNotifications,
	host *fleet.Host,
	appConfig *fleet.AppConfig,
	diskEncryptionConfigured bool,
	isConnectedToFleetMDM bool,
	mdmInfo *fleet.HostMDM,
) error {
	anyMDMConfigured := appConfig.MDM.EnabledAndConfigured || appConfig.MDM.WindowsEnabledAndConfigured
	if !anyMDMConfigured ||
		!isConnectedToFleetMDM ||
		!host.IsOsqueryEnrolled() ||
		!diskEncryptionConfigured {
		return nil
	}

	encryptionKey, err := svc.ds.GetHostDiskEncryptionKey(ctx, host.ID)
	if err != nil {
		if !fleet.IsNotFound(err) {
			return ctxerr.Wrap(ctx, err, "fetching host disk encryption key")
		}
	}

	switch host.FleetPlatform() {
	case "darwin":
		mp, ok := capabilities.FromContext(ctx)
		if !ok {
			svc.logger.DebugContext(ctx, "no capabilities in context, skipping disk encryption notification")
			return nil
		}

		if !mp.Has(fleet.CapabilityEscrowBuddy) {
			svc.logger.DebugContext(ctx, "host doesn't support Escrow Buddy, skipping disk encryption notification", "host_uuid", host.UUID)
			return nil
		}

		notifs.RotateDiskEncryptionKey = encryptionKey != nil && encryptionKey.Decryptable != nil && !*encryptionKey.Decryptable
	case "windows":
		isServer := mdmInfo != nil && mdmInfo.IsServer
		needsEncryption := host.DiskEncryptionEnabled != nil && !*host.DiskEncryptionEnabled
		keyWasDecrypted := encryptionKey != nil && encryptionKey.Decryptable != nil && *encryptionKey.Decryptable
		encryptedWithoutKey := host.DiskEncryptionEnabled != nil && *host.DiskEncryptionEnabled && !keyWasDecrypted
		notifs.EnforceBitLockerEncryption = !isServer &&
			mdmInfo != nil &&
			(needsEncryption || encryptedWithoutKey)
	}

	return nil
}

// filterExtensionsForHost filters a extensions configuration depending on the host platform and label membership.
//
// If all extensions are filtered, then it returns (nil, nil) (Orbit expects empty extensions if there
// are no extensions for the host.)
func (svc *Service) filterExtensionsForHost(ctx context.Context, extensions json.RawMessage, host *fleet.Host) (json.RawMessage, error) {
	if len(extensions) == 0 {
		return nil, nil
	}
	var extensionsInfo fleet.Extensions
	if err := json.Unmarshal(extensions, &extensionsInfo); err != nil {
		return nil, ctxerr.Wrap(ctx, err, "unmarshal extensions config")
	}

	// Filter the extensions by platform.
	extensionsInfo.FilterByHostPlatform(host.Platform, host.CPUType)

	// Filter the extensions by labels (premium only feature).
	if license, _ := license.FromContext(ctx); license != nil && license.IsPremium() {
		for extensionName, extensionInfo := range extensionsInfo {
			hostIsMemberOfAllLabels, err := svc.ds.HostMemberOfAllLabels(ctx, host.ID, extensionInfo.Labels)
			if err != nil {
				return nil, ctxerr.Wrap(ctx, err, "check host labels")
			}
			if hostIsMemberOfAllLabels {
				// Do not filter out, but there's no need to send the label names to the devices.
				extensionInfo.Labels = nil
				extensionsInfo[extensionName] = extensionInfo
			} else {
				delete(extensionsInfo, extensionName)
			}
		}
	}
	// Orbit expects empty message if no extensions apply.
	if len(extensionsInfo) == 0 {
		return nil, nil
	}
	extensionsFiltered, err := json.Marshal(extensionsInfo)
	if err != nil {
		return nil, ctxerr.Wrap(ctx, err, "marshal extensions config")
	}
	return extensionsFiltered, nil
}

/////////////////////////////////////////////////////////////////////////////////
// Ping orbit endpoint
/////////////////////////////////////////////////////////////////////////////////

// orbitPingResponse wraps the fleet type to add HijackRender.
type orbitPingResponse struct {
	fleet.OrbitPingResponse
}

func (r orbitPingResponse) HijackRender(ctx context.Context, w http.ResponseWriter) {
	writeCapabilitiesHeader(w, fleet.GetServerOrbitCapabilities())
}

// NOTE: we're intentionally not reading the capabilities header in this
// endpoint as is unauthenticated and we don't want to trust whatever comes in
// there.
func orbitPingEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	svc.DisableAuthForPing(ctx)
	return orbitPingResponse{}, nil
}

/////////////////////////////////////////////////////////////////////////////////
// SetOrUpdateDeviceToken endpoint
/////////////////////////////////////////////////////////////////////////////////

func setOrUpdateDeviceTokenEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.SetOrUpdateDeviceTokenRequest)
	if err := svc.SetOrUpdateDeviceAuthToken(ctx, req.DeviceAuthToken); err != nil {
		return fleet.SetOrUpdateDeviceTokenResponse{Err: err}, nil
	}
	return fleet.SetOrUpdateDeviceTokenResponse{}, nil
}

func (svc *Service) SetOrUpdateDeviceAuthToken(ctx context.Context, deviceAuthToken string) error {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	if len(deviceAuthToken) == 0 {
		return badRequest("device auth token cannot be empty")
	}

	if url.QueryEscape(deviceAuthToken) != deviceAuthToken {
		return badRequest("device auth token contains invalid characters")
	}

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		return newOsqueryError("internal error: missing host from request context")
	}

	if err := svc.ds.SetOrUpdateDeviceAuthToken(ctx, host.ID, deviceAuthToken); err != nil {
		if errors.As(err, &fleet.ConflictError{}) {
			return err
		}
		return newOsqueryError(fmt.Sprintf("internal error: failed to set or update device auth token: %s", err))
	}

	return nil
}

/////////////////////////////////////////////////////////////////////////////////
// Get Orbit pending script execution request
/////////////////////////////////////////////////////////////////////////////////

func getOrbitScriptEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.OrbitGetScriptRequest)
	script, err := svc.GetHostScript(ctx, req.ExecutionID)
	if err != nil {
		return fleet.OrbitGetScriptResponse{Err: err}, nil
	}
	return fleet.OrbitGetScriptResponse{HostScriptResult: script}, nil
}

func (svc *Service) GetHostScript(ctx context.Context, execID string) (*fleet.HostScriptResult, error) {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		return nil, fleet.OrbitError{Message: "internal error: missing host from request context"}
	}

	// get the script's details
	script, err := svc.ds.GetHostScriptExecutionResult(ctx, execID)
	if err != nil {
		return nil, err
	}
	// ensure it cannot get access to a different host's script
	if script.HostID != host.ID {
		return nil, ctxerr.Wrap(ctx, newNotFoundError(), "no script found for this host")
	}

	// We expose secret variables in the script content to the host. The exposed secrets are only intended to go to the device and not accessible via the UI/API.
	script.ScriptContents, err = svc.ds.ExpandEmbeddedSecrets(ctx, script.ScriptContents)
	if err != nil {
		// This error should never occur because we validate secret variables on script upload.
		return nil, ctxerr.Wrap(ctx, err, fmt.Sprintf("expand embedded secrets for host %d and script %s", host.ID, execID))
	}

	return script, nil
}

/////////////////////////////////////////////////////////////////////////////////
// Post Orbit script execution result
/////////////////////////////////////////////////////////////////////////////////

func postOrbitScriptResultEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.OrbitPostScriptResultRequest)
	if err := svc.SaveHostScriptResult(ctx, req.HostScriptResultPayload); err != nil {
		return fleet.OrbitPostScriptResultResponse{Err: err}, nil
	}
	return fleet.OrbitPostScriptResultResponse{}, nil
}

func (svc *Service) SaveHostScriptResult(ctx context.Context, result *fleet.HostScriptResultPayload) error {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		return fleet.OrbitError{Message: "internal error: missing host from request context"}
	}
	if result == nil {
		return ctxerr.Wrap(ctx, &fleet.BadRequestError{Message: "missing script result"}, "save host script result")
	}

	// always use the authenticated host's ID as host_id
	result.HostID = host.ID

	// Calculate attempt_number for policy automation retries by counting existing attempts
	attemptNumber, err := svc.getPolicyAutomationScriptAttemptNumber(ctx, host, result.ExecutionID)
	if err != nil {
		return err
	}

	hsr, action, err := svc.ds.SetHostScriptExecutionResult(ctx, result, attemptNumber)
	if err != nil {
		return ctxerr.Wrap(ctx, err, "save host script result")
	}

	// FIXME: datastore implementation of action seems rather brittle, can it be refactored?
	var fromSetupExperience bool
	if action == "" && fleet.IsSetupExperienceSupported(host.Platform) {
		// this might be a setup experience script result
		if updated, err := maybeUpdateSetupExperienceStatus(ctx, svc.ds, fleet.SetupExperienceScriptResult{
			HostUUID:    host.UUID,
			ExecutionID: result.ExecutionID,
			ExitCode:    result.ExitCode,
		}, svc.NewActivity); err != nil {
			return ctxerr.Wrap(ctx, err, "update setup experience status")
		} else if updated {
			svc.logger.DebugContext(ctx, "setup experience script result updated", "host_uuid", host.UUID, "execution_id", result.ExecutionID)
			fromSetupExperience = true
			_, err := svc.EnterpriseOverrides.SetupExperienceNextStep(ctx, host)
			if err != nil {
				return ctxerr.Wrap(ctx, err, "getting next step for host setup experience")
			}
		}
	}

	// don't create a "past" activity if the result was for a canceled activity
	if hsr != nil && !hsr.Canceled {
		var user *fleet.User
		if hsr.UserID != nil {
			user, err = svc.ds.UserByID(ctx, *hsr.UserID)
			if err != nil {
				return ctxerr.Wrap(ctx, err, "get host script execution user")
			}
		}
		var scriptName string

		switch {
		case hsr.ScriptID != nil:
			scr, err := svc.ds.Script(ctx, *hsr.ScriptID)
			if err != nil {
				return ctxerr.Wrap(ctx, err, "get saved script")
			}
			scriptName = scr.Name
		case hsr.SetupExperienceScriptID != nil:
			scr, err := svc.ds.GetSetupExperienceScriptByID(ctx, *hsr.SetupExperienceScriptID)
			if err != nil {
				return ctxerr.Wrap(ctx, err, "get setup experience script")
			}

			scriptName = scr.Name
		}

		switch action {
		case "uninstall":
			softwareTitleName, selfService, err := svc.ds.GetDetailsForUninstallFromExecutionID(ctx, hsr.ExecutionID)
			if err != nil {
				return ctxerr.Wrap(ctx, err, "get software title from execution ID")
			}
			activityStatus := "failed"
			if hsr.ExitCode != nil && *hsr.ExitCode == 0 {
				activityStatus = "uninstalled"
			}
			if err := svc.NewActivity(
				ctx,
				user,
				fleet.ActivityTypeUninstalledSoftware{
					HostID:          host.ID,
					HostDisplayName: host.DisplayName(),
					SoftwareTitle:   softwareTitleName,
					ExecutionID:     hsr.ExecutionID,
					Status:          activityStatus,
					SelfService:     selfService,
				},
			); err != nil {
				return ctxerr.Wrap(ctx, err, "create activity for script execution request")
			}

			// lastly, queue a vitals refetch so we get a proper view of inventory from osquery
			if activityStatus == "uninstalled" {
				if err := svc.ds.UpdateHostRefetchRequested(ctx, host.ID, true); err != nil {
					return ctxerr.Wrap(ctx, err, "queue host vitals refetch")
				}
			}
		case "wipe_ref":
			// a successful wipe means the host has been erased, so any other
			// upcoming activities queued behind the wipe will never run -
			// cancel them silently before falling through to record the
			// "ran script" activity for the wipe itself.
			if hsr.ExitCode != nil && *hsr.ExitCode == 0 {
				if _, err := svc.ds.BatchCancelAllHostUpcomingActivities(ctx, host.ID); err != nil {
					return ctxerr.Wrap(ctx, err, "cancel upcoming activities after wipe")
				}
			}
			fallthrough
		default:
			// TODO(sarah): We may need to special case lock/unlock script results here?
			var policyName *string
			shouldCreateActivity := true
			if hsr.PolicyID != nil {
				if policy, err := svc.ds.PolicyLite(ctx, *hsr.PolicyID); err == nil {
					policyName = &policy.Name // fall back to blank policy name if we can't retrieve the policy
				}

				// Suppress activity for policy automation retires
				if hsr.AttemptNumber != nil {
					scriptFailed := hsr.ExitCode == nil || *hsr.ExitCode != 0
					if scriptFailed && *hsr.AttemptNumber < fleet.MaxPolicyAutomationRetries {
						shouldCreateActivity = false
					}
				}
			}

			if shouldCreateActivity {
				if err := svc.NewActivity(
					ctx,
					user,
					fleet.ActivityTypeRanScript{
						HostID:              host.ID,
						HostDisplayName:     host.DisplayName(),
						ScriptExecutionID:   hsr.ExecutionID,
						BatchExecutionID:    hsr.BatchExecutionID,
						ScriptName:          scriptName,
						Async:               !hsr.SyncRequest,
						PolicyID:            hsr.PolicyID,
						PolicyName:          policyName,
						FromSetupExperience: fromSetupExperience,
					},
				); err != nil {
					return ctxerr.Wrap(ctx, err, "create activity for script execution request")
				}
			}
		}
	}

	// If this is a policy automation script that failed, maybe retry
	if hsr != nil && hsr.PolicyID != nil && hsr.ScriptID != nil {
		scriptFailed := hsr.ExitCode == nil || *hsr.ExitCode != 0
		if scriptFailed {
			shouldRetry, err := svc.shouldRetryPolicyAutomationScript(ctx, host, hsr)
			if err != nil {
				svc.logger.ErrorContext(ctx,
					"failed to check if policy automation script should retry",
					"host_id", host.ID,
					"policy_id", *hsr.PolicyID,
					"err", err,
				)
			} else if shouldRetry {
				if err := svc.retryPolicyAutomationScript(ctx, host, hsr); err != nil {
					svc.logger.ErrorContext(ctx,
						"failed to queue policy automation script retry",
						"host_id", host.ID,
						"policy_id", *hsr.PolicyID,
						"err", err,
					)
				}
			}
		}
	}

	return nil
}

/////////////////////////////////////////////////////////////////////////////////
// Post Orbit device mapping (custom email)
/////////////////////////////////////////////////////////////////////////////////

func putOrbitDeviceMappingEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.OrbitPutDeviceMappingRequest)

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		err := newOsqueryError("internal error: missing host from request context")
		return fleet.OrbitPutDeviceMappingResponse{Err: err}, nil
	}

	_, err := svc.SetHostDeviceMapping(ctx, host.ID, req.Email, fleet.DeviceMappingCustomReplacement)
	return fleet.OrbitPutDeviceMappingResponse{Err: err}, nil
}

/////////////////////////////////////////////////////////////////////////////////
// Post Orbit disk encryption key
/////////////////////////////////////////////////////////////////////////////////

func postOrbitDiskEncryptionKeyEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.OrbitPostDiskEncryptionKeyRequest)
	if err := svc.SetOrUpdateDiskEncryptionKey(ctx, string(req.EncryptionKey), req.ClientError); err != nil {
		return fleet.OrbitPostDiskEncryptionKeyResponse{Err: err}, nil
	}
	return fleet.OrbitPostDiskEncryptionKeyResponse{}, nil
}

func (svc *Service) SetOrUpdateDiskEncryptionKey(ctx context.Context, encryptionKey, clientError string) error {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		return newOsqueryError("internal error: missing host from request context")
	}

	connected, err := svc.ds.IsHostConnectedToFleetMDM(ctx, host)
	if err != nil {
		return ctxerr.Wrap(ctx, err, "checking if host is connected to Fleet")
	}

	if !connected {
		return badRequest("host is not enrolled with fleet")
	}

	// Only archive the key if disk encryption is enabled for this host (team/globally)
	if !osquery_utils.IsDiskEncryptionEnabledForHost(ctx, svc.logger, svc.ds, host) {
		svc.logger.DebugContext(ctx,
			"skipping key archival, disk encryption not enabled for host team/globally",
			"host_id", host.ID,
		)
		return nil
	}

	var (
		encryptedEncryptionKey string
		decryptable            *bool
	)

	// only set the encryption key if there was no client error
	if clientError == "" && encryptionKey != "" {
		wstepCert, _, _, err := svc.config.MDM.MicrosoftWSTEP()
		if err != nil {
			// should never return an error because the WSTEP is first parsed and
			// cached at the start of the fleet serve process.
			return ctxerr.Wrap(ctx, err, "get WSTEP certificate")
		}
		enc, err := microsoft_mdm.Encrypt(encryptionKey, wstepCert.Leaf)
		if err != nil {
			return ctxerr.Wrap(ctx, err, "encrypt the key with WSTEP certificate")
		}
		encryptedEncryptionKey = enc
		decryptable = ptr.Bool(true)
	}

	keyArchived, err := svc.ds.SetOrUpdateHostDiskEncryptionKey(ctx, host, encryptedEncryptionKey, clientError, decryptable)
	if err != nil {
		return ctxerr.Wrap(ctx, err, "set or update disk encryption key")
	}

	// We only want to record the activity if the key was successfully archived.
	if !keyArchived {
		return nil
	}
	if err := svc.NewActivity(
		ctx,
		nil,
		fleet.ActivityTypeEscrowedDiskEncryptionKey{
			HostID:          host.ID,
			HostDisplayName: host.DisplayName(),
		},
	); err != nil {
		// OK: this is not critical to the operation of the endpoint
		svc.logger.ErrorContext(ctx,
			"record fleet disk encryption key escrowed activity",
			"err", err,
		)
		ctxerr.Handle(ctx, err)
	}

	return nil
}

/////////////////////////////////////////////////////////////////////////////////
// Post Orbit LUKS (Linux disk encryption) data
/////////////////////////////////////////////////////////////////////////////////

func postOrbitLUKSEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.OrbitPostLUKSRequest)
	if err := svc.EscrowLUKSData(ctx, req.Passphrase, req.Salt, req.KeySlot, req.ClientError); err != nil {
		return fleet.OrbitPostLUKSResponse{Err: err}, nil
	}
	return fleet.OrbitPostLUKSResponse{}, nil
}

func (svc *Service) EscrowLUKSData(ctx context.Context, passphrase string, salt string, keySlot *uint, clientError string) error {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		return newOsqueryError("internal error: missing host from request context")
	}

	if clientError != "" {
		return svc.ds.ReportEscrowError(ctx, host.ID, clientError)
	}

	// Only archive the key if disk encryption is enabled for this host (team/globally)
	if !osquery_utils.IsDiskEncryptionEnabledForHost(ctx, svc.logger, svc.ds, host) {
		svc.logger.DebugContext(ctx,
			"skipping LUKS key archival, disk encryption not enabled for host team/globally",
			"host_id", host.ID,
		)
		return nil
	}

	encryptedPassphrase, encryptedSalt, validatedKeySlot, err := svc.validateAndEncrypt(ctx, passphrase, salt, keySlot)
	if err != nil {
		_ = svc.ds.ReportEscrowError(ctx, host.ID, err.Error())
		return err
	}

	keyArchived, err := svc.ds.SaveLUKSData(ctx, host, encryptedPassphrase, encryptedSalt, validatedKeySlot)
	if err != nil {
		return err
	}

	// When only want to record a new activity if the current key was archived ...
	if !keyArchived {
		return nil
	}
	if err := svc.NewActivity(
		ctx,
		nil,
		fleet.ActivityTypeEscrowedDiskEncryptionKey{
			HostID:          host.ID,
			HostDisplayName: host.DisplayName(),
		},
	); err != nil {
		// OK: this is not critical to the operation of the endpoint
		svc.logger.ErrorContext(ctx,
			"record fleet disk encryption key escrowed activity",
			"err", err,
		)
		ctxerr.Handle(ctx, err)
	}

	return nil
}

func (svc *Service) validateAndEncrypt(ctx context.Context, passphrase string, salt string, keySlot *uint) (encryptedPassphrase string, encryptedSalt string, validatedKeySlot uint, err error) {
	if passphrase == "" || salt == "" || keySlot == nil {
		return "", "", 0, badRequest("passphrase, salt, and key_slot must be provided to escrow LUKS data")
	}
	if svc.config.Server.PrivateKey == "" {
		return "", "", 0, newOsqueryError("internal error: missing server private key")
	}

	encryptedPassphrase, err = mdm.EncryptAndEncode(passphrase, svc.config.Server.PrivateKey)
	if err != nil {
		return "", "", 0, ctxerr.Wrap(ctx, err, "internal error: could not encrypt LUKS data")
	}
	encryptedSalt, err = mdm.EncryptAndEncode(salt, svc.config.Server.PrivateKey)
	if err != nil {
		return "", "", 0, ctxerr.Wrap(ctx, err, "internal error: could not encrypt LUKS data")
	}

	return encryptedPassphrase, encryptedSalt, *keySlot, nil
}

/////////////////////////////////////////////////////////////////////////////////
// Get Orbit pending software installations
/////////////////////////////////////////////////////////////////////////////////

func getOrbitSoftwareInstallDetails(ctx context.Context, request any, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.OrbitGetSoftwareInstallRequest)
	details, err := svc.GetSoftwareInstallDetails(ctx, req.InstallUUID)
	if err != nil {
		return fleet.OrbitGetSoftwareInstallResponse{Err: err}, nil
	}

	return fleet.OrbitGetSoftwareInstallResponse{SoftwareInstallDetails: details}, nil
}

func (svc *Service) GetSoftwareInstallDetails(ctx context.Context, installUUID string) (*fleet.SoftwareInstallDetails, error) {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		return nil, fleet.OrbitError{Message: "internal error: missing host from request context"}
	}

	details, err := svc.ds.GetSoftwareInstallDetails(ctx, installUUID)
	if err != nil {
		return nil, err
	}

	// ensure it cannot get access to a different host's installers
	if details.HostID != host.ID {
		return nil, ctxerr.Wrap(ctx, newNotFoundError(), "no installer found for this host")
	}
	return details, nil
}

// Download Orbit software installer request
/////////////////////////////////////////////////////////////////////////////////

func orbitDownloadSoftwareInstallerEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.OrbitDownloadSoftwareInstallerRequest)

	downloadRequested := req.Alt == "media"
	if !downloadRequested {
		// TODO: confirm error handling
		return orbitDownloadSoftwareInstallerResponse{Err: &fleet.BadRequestError{Message: "only alt=media is supported"}}, nil
	}

	p, err := svc.OrbitDownloadSoftwareInstaller(ctx, req.InstallerID)
	if err != nil {
		return orbitDownloadSoftwareInstallerResponse{Err: err}, nil
	}
	return orbitDownloadSoftwareInstallerResponse{payload: p}, nil
}

func (svc *Service) OrbitDownloadSoftwareInstaller(ctx context.Context, installerID uint) (*fleet.DownloadSoftwareInstallerPayload, error) {
	// skipauth: No authorization check needed due to implementation returning
	// only license error.
	svc.authz.SkipAuthorization(ctx)

	return nil, fleet.ErrMissingLicense
}

/////////////////////////////////////////////////////////////////////////////////
// Post Orbit software install result
/////////////////////////////////////////////////////////////////////////////////

func postOrbitSoftwareInstallResultEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.OrbitPostSoftwareInstallResultRequest)
	if err := svc.SaveHostSoftwareInstallResult(ctx, req.HostSoftwareInstallResultPayload); err != nil {
		return fleet.OrbitPostSoftwareInstallResultResponse{Err: err}, nil
	}
	return fleet.OrbitPostSoftwareInstallResultResponse{}, nil
}

func (svc *Service) SaveHostSoftwareInstallResult(ctx context.Context, result *fleet.HostSoftwareInstallResultPayload) error {
	// this is not a user-authenticated endpoint
	svc.authz.SkipAuthorization(ctx)

	host, ok := hostctx.FromContext(ctx)
	if !ok {
		return newOsqueryError("internal error: missing host from request context")
	}

	// always use the authenticated host's ID as host_id
	result.HostID = host.ID

	// If this is an intermediate failure that will be retried, handle it specially
	if result.RetriesRemaining > 0 {
		// Create a record while keeping the original pending
		_, err := svc.ds.CreateIntermediateInstallFailureRecord(ctx, result)
		if err != nil {
			return ctxerr.Wrap(ctx, err, "save intermediate install failure")
		}

		// Don't create activities for intermediate failures during setup experience.
		// Only the final result (RetriesRemaining == 0) should create an activity.
		// This prevents multiple activity items from appearing when a package fails
		// during setup experience with retries enabled.
		// See https://github.com/fleetdm/fleet/issues/34818

		// Don't update setup experience status for intermediate failures
		return nil
	}

	// Calculate attempt_number for retries by counting existing attempts
	attemptNumber, err := svc.getSoftwareInstallerAttemptNumber(ctx, host, result.InstallUUID)
	if err != nil {
		return err
	}

	// Check if a non-policy install failure will be retried so we can skip
	// updating setup experience status during intermediate retries.
	willRetryNonPolicyOnFailure := false
	if attemptNumber != nil && *attemptNumber < fleet.MaxSoftwareInstallAttempts && result.Status() == fleet.SoftwareInstallFailed {
		currentInstall, checkErr := svc.ds.GetSoftwareInstallResults(ctx, result.InstallUUID)
		if checkErr == nil && currentInstall != nil && currentInstall.PolicyID == nil {
			willRetryNonPolicyOnFailure = true
		}
	}

	var fromSetupExperience bool
	if fleet.IsSetupExperienceSupported(host.Platform) && !willRetryNonPolicyOnFailure {
		// This might be a setup experience software install result, so we attempt to update the
		// "Setup experience" status for that item.
		hostUUID, err := fleet.HostUUIDForSetupExperience(host)
		if err != nil {
			return ctxerr.Wrap(ctx, err, "failed to get host's UUID for the setup experience")
		}
		if updated, err := maybeUpdateSetupExperienceStatus(ctx, svc.ds, fleet.SetupExperienceSoftwareInstallResult{
			HostUUID:        hostUUID,
			ExecutionID:     result.InstallUUID,
			InstallerStatus: result.Status(),
		}, svc.NewActivity); err != nil {
			return ctxerr.Wrap(ctx, err, "update setup experience status")
		} else if updated {
			svc.logger.DebugContext(ctx,
				"setup experience software install result updated",
				"host_uuid", hostUUID,
				"execution_id", result.InstallUUID,
			)
			fromSetupExperience = true
			// We need to trigger the next step to properly support setup experience on Linux.
			// On Linux, users can skip the setup experience by closing the "My device" page.
			if _, err := svc.EnterpriseOverrides.SetupExperienceNextStep(ctx, host); err != nil {
				return ctxerr.Wrap(ctx, err, "getting next step for host setup experience")
			}
		}
	}

	installWasCanceled, err := svc.ds.SetHostSoftwareInstallResult(ctx, result, attemptNumber)
	if err != nil {
		return ctxerr.Wrap(ctx, err, "save host software installation result")
	}

	// do not create a "past" activity if the status is not terminal or if the activity
	// was canceled.
	if status := result.Status(); status != fleet.SoftwareInstallPending && !installWasCanceled {
		// Force read from primary to avoid replication lag issues where attempt_number might be NULL
		ctx = ctxdb.RequirePrimary(ctx, true)
		hsi, err := svc.ds.GetSoftwareInstallResults(ctx, result.InstallUUID)
		if err != nil {
			return ctxerr.Wrap(ctx, err, "get host software installation result information")
		}

		// Self-Service installs, and installs made by automations, will have a nil author for the activity.
		var user *fleet.User
		if !hsi.SelfService && hsi.UserID != nil {
			user, err = svc.ds.UserByID(ctx, *hsi.UserID)
			if err != nil {
				return ctxerr.Wrap(ctx, err, "get host software installation user")
			}
		}

		var policyName *string
		shouldCreateActivity := true
		if hsi.PolicyID != nil {
			if policy, err := svc.ds.PolicyLite(ctx, *hsi.PolicyID); err == nil && policy != nil {
				policyName = &policy.Name // fall back to blank policy name if we can't retrieve the policy
			}

			if status == fleet.SoftwareInstallFailed {
				shouldRetry, err := svc.shouldRetryPolicyAutomationSoftwareInstall(ctx, host, hsi)
				if err != nil {
					svc.logger.ErrorContext(ctx,
						"failed to check if policy automation software install should retry",
						"host_id", host.ID,
						"policy_id", *hsi.PolicyID,
						"err", err,
					)
				} else if shouldRetry {
					if err := svc.retryPolicyAutomationSoftwareInstall(ctx, host, hsi); err != nil {
						svc.logger.ErrorContext(ctx,
							"failed to queue policy automation software install retry",
							"host_id", host.ID,
							"policy_id", *hsi.PolicyID,
							"err", err,
						)
					}
				}

				// Only create activity on final
				if hsi.AttemptNumber != nil {
					if *hsi.AttemptNumber < fleet.MaxPolicyAutomationRetries {
						shouldCreateActivity = false
					}
				}
			}
		}

		// Non-policy install retry (host details, self-service, setup experience).
		// Errors here are logged but do not abort the handler. The primary
		// action, recording the install result from the device, must succeed
		// regardless of whether a retry can be scheduled. If retry scheduling
		// fails, the install is marked as failed (no retry) and the admin can
		// manually re-trigger.
		if hsi.PolicyID == nil && status == fleet.SoftwareInstallFailed {
			shouldRetry, retryErr := svc.shouldRetrySoftwareInstall(ctx, hsi)
			if retryErr != nil {
				svc.logger.ErrorContext(ctx,
					"failed to check if software install should retry",
					"host_id", host.ID,
					"install_uuid", result.InstallUUID,
					"err", retryErr,
				)
			} else if shouldRetry {
				if retryErr := svc.retrySoftwareInstall(ctx, host, hsi, fromSetupExperience); retryErr != nil {
					svc.logger.ErrorContext(ctx,
						"failed to queue software install retry",
						"host_id", host.ID,
						"install_uuid", result.InstallUUID,
						"err", retryErr,
					)
				}
			}
		}

		if shouldCreateActivity {
			if err := svc.NewActivity(
				ctx,
				user,
				fleet.ActivityTypeInstalledSoftware{
					HostID:              host.ID,
					HostDisplayName:     host.DisplayName(),
					SoftwareTitle:       hsi.SoftwareTitle,
					SoftwarePackage:     hsi.SoftwarePackage,
					InstallUUID:         result.InstallUUID,
					Status:              string(status),
					Source:              hsi.Source,
					SelfService:         hsi.SelfService,
					PolicyID:            hsi.PolicyID,
					PolicyName:          policyName,
					FromSetupExperience: fromSetupExperience,
				},
			); err != nil {
				return ctxerr.Wrap(ctx, err, "create activity for software installation")
			}
		}

		// lastly, queue a vitals refetch so we get a proper view of inventory from osquery
		if status == fleet.SoftwareInstalled {
			if err := svc.ds.UpdateHostRefetchRequested(ctx, host.ID, true); err != nil {
				return ctxerr.Wrap(ctx, err, "queue host vitals refetch")
			}
		}
	}
	return nil
}

// shouldRetryPolicyAutomationSoftwareInstall checks if a failed policy automation software install should be retried.
// Returns true if retry should be queued
func (svc *Service) shouldRetryPolicyAutomationSoftwareInstall(ctx context.Context, host *fleet.Host, hsi *fleet.HostSoftwareInstallerResult) (bool, error) {
	if hsi.AttemptNumber == nil {
		// should not happen
		return false, ctxerr.New(ctx, "attempt_number is nil for policy automation install")
	}

	currentAttempt := *hsi.AttemptNumber

	if currentAttempt >= fleet.MaxPolicyAutomationRetries {
		return false, nil
	}

	// Check if policy is failing for this host
	policyFailing, err := svc.ds.IsPolicyFailing(ctx, *hsi.PolicyID, host.ID)
	if err != nil {
		return false, ctxerr.Wrap(ctx, err, "check if policy is failing")
	}

	return policyFailing, nil
}

// retryPolicyAutomationSoftwareInstall queues a retry for a policy automation software install.
func (svc *Service) retryPolicyAutomationSoftwareInstall(ctx context.Context, host *fleet.Host, hsi *fleet.HostSoftwareInstallerResult) error {
	svc.logger.InfoContext(ctx,
		"queuing policy automation software install retry",
		"host_id", host.ID,
		"policy_id", *hsi.PolicyID,
		"software_installer_id", *hsi.SoftwareInstallerID,
		"current_attempt", *hsi.AttemptNumber,
	)
	_, err := svc.ds.InsertSoftwareInstallRequest(ctx, host.ID, *hsi.SoftwareInstallerID, fleet.HostSoftwareInstallOptions{
		PolicyID: hsi.PolicyID,
	})
	return err
}

// shouldRetrySoftwareInstall checks if a failed non-policy software install should be retried.
func (svc *Service) shouldRetrySoftwareInstall(ctx context.Context, hsi *fleet.HostSoftwareInstallerResult) (bool, error) {
	if hsi.AttemptNumber == nil {
		return false, nil
	}
	return *hsi.AttemptNumber < fleet.MaxSoftwareInstallAttempts, nil
}

// retrySoftwareInstall queues a retry for a non-policy software install.
func (svc *Service) retrySoftwareInstall(ctx context.Context, host *fleet.Host, hsi *fleet.HostSoftwareInstallerResult, fromSetupExperience bool) error {
	svc.logger.InfoContext(ctx,
		"queuing software install retry",
		"host_id", host.ID,
		"software_installer_id", *hsi.SoftwareInstallerID,
		"self_service", hsi.SelfService,
		"current_attempt", *hsi.AttemptNumber,
	)
	_, err := svc.ds.InsertSoftwareInstallRequest(ctx, host.ID, *hsi.SoftwareInstallerID, fleet.HostSoftwareInstallOptions{
		SelfService:        hsi.SelfService,
		UserID:             hsi.UserID,
		ForSetupExperience: fromSetupExperience,
		WithRetries:        true,
	})
	return err
}

// shouldRetryPolicyAutomationScript checks if a failed policy automation script should be retried.
// Returns true if retry should be queued
func (svc *Service) shouldRetryPolicyAutomationScript(ctx context.Context, host *fleet.Host, hsr *fleet.HostScriptResult) (bool, error) {
	if hsr.AttemptNumber == nil {
		// should not happen
		return false, ctxerr.New(ctx, "attempt_number is nil for policy automation script")
	}

	currentAttempt := *hsr.AttemptNumber

	if currentAttempt >= fleet.MaxPolicyAutomationRetries {
		return false, nil
	}

	// Check if policy is failing for this host
	policyFailing, err := svc.ds.IsPolicyFailing(ctx, *hsr.PolicyID, host.ID)
	if err != nil {
		return false, ctxerr.Wrap(ctx, err, "check if policy is failing")
	}

	return policyFailing, nil
}

// retryPolicyAutomationScript queues a retry for a policy automation script.
func (svc *Service) retryPolicyAutomationScript(ctx context.Context, host *fleet.Host, hsr *fleet.HostScriptResult) error {
	svc.logger.InfoContext(ctx,
		"queuing policy automation script retry",
		"host_id", host.ID,
		"policy_id", *hsr.PolicyID,
		"script_id", *hsr.ScriptID,
		"current_attempt", *hsr.AttemptNumber,
	)
	_, err := svc.ds.NewHostScriptExecutionRequest(ctx, &fleet.HostScriptRequestPayload{
		HostID:         host.ID,
		ScriptID:       hsr.ScriptID,
		PolicyID:       hsr.PolicyID,
		ScriptContents: hsr.ScriptContents,
	})
	return err
}

// getPolicyAutomationScriptAttemptNumber calculates the attempt number for a policy automation script.
// Returns nil for manual script runs (not triggered by policy automation).
func (svc *Service) getPolicyAutomationScriptAttemptNumber(ctx context.Context, host *fleet.Host, executionID string) (*int, error) {
	// First, check if this script execution already exists and has policy_id
	// (to know if this is a policy automation)
	existingResult, err := svc.ds.GetHostScriptExecutionResult(ctx, executionID)
	if err != nil && !fleet.IsNotFound(err) {
		return nil, ctxerr.Wrap(ctx, err, "get existing script result for attempt number calculation")
	}

	// Only calculate attempt_number for policy automation scripts
	if existingResult != nil && existingResult.PolicyID != nil && existingResult.ScriptID != nil {
		count, err := svc.ds.CountHostScriptAttempts(ctx, host.ID, *existingResult.ScriptID, *existingResult.PolicyID)
		if err != nil {
			return nil, ctxerr.Wrap(ctx, err, "count previous script attempts")
		}
		return &count, nil // count already includes current row since it was created when queued
	}

	return nil, nil // nil for manual runs
}

// getSoftwareInstallerAttemptNumber calculates the attempt number for a software install.
// Returns nil for installs that don't have a software_installer_id.
func (svc *Service) getSoftwareInstallerAttemptNumber(ctx context.Context, host *fleet.Host, installUUID string) (*int, error) {
	currentInstall, err := svc.ds.GetSoftwareInstallResults(ctx, installUUID)
	if err != nil && !fleet.IsNotFound(err) {
		return nil, ctxerr.Wrap(ctx, err, "get current install info for attempt number calculation")
	}

	if currentInstall == nil || currentInstall.SoftwareInstallerID == nil {
		return nil, nil
	}

	// Policy automation installs
	if currentInstall.PolicyID != nil {
		count, err := svc.ds.CountHostSoftwareInstallAttempts(ctx, host.ID, *currentInstall.SoftwareInstallerID, *currentInstall.PolicyID)
		if err != nil {
			return nil, ctxerr.Wrap(ctx, err, "count previous policy install attempts")
		}
		return &count, nil
	}

	// Non-policy installs (host details, self-service, setup experience):
	// attempt_number is set at activation time for retry-eligible installs
	// (those created with WithRetries=true). If nil, this install was not
	// created with retry support.
	return currentInstall.AttemptNumber, nil
}

/////////////////////////////////////////////////////////////////////////////////
// Get Orbit setup experience status
/////////////////////////////////////////////////////////////////////////////////

func getOrbitSetupExperienceStatusEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	req := request.(*fleet.GetOrbitSetupExperienceStatusRequest)
	results, err := svc.GetOrbitSetupExperienceStatus(ctx, req.OrbitNodeKey, req.ForceRelease, req.ResetFailedSetupSteps)
	if err != nil {
		return &fleet.GetOrbitSetupExperienceStatusResponse{Err: err}, nil
	}
	return &fleet.GetOrbitSetupExperienceStatusResponse{Results: results}, nil
}

func (svc *Service) GetOrbitSetupExperienceStatus(ctx context.Context, orbitNodeKey string, forceRelease bool, resetFailedSetupSteps bool) (*fleet.SetupExperienceStatusPayload, error) {
	// skipauth: No authorization check needed due to implementation returning
	// only license error.
	svc.authz.SkipAuthorization(ctx)

	return nil, fleet.ErrMissingLicense
}

/////////////////////////////////////////////////////////////////////////////////
// Setup experience init
/////////////////////////////////////////////////////////////////////////////////

func orbitSetupExperienceInitEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (fleet.Errorer, error) {
	_, ok := request.(*fleet.OrbitSetupExperienceInitRequest)
	if !ok {
		return nil, fmt.Errorf("internal error: invalid request type: %T", request)
	}
	result, err := svc.SetupExperienceInit(ctx)
	if err != nil {
		return fleet.OrbitSetupExperienceInitResponse{Err: err}, nil
	}
	return fleet.OrbitSetupExperienceInitResponse{
		Result: *result,
	}, nil
}

func (svc *Service) SetupExperienceInit(ctx context.Context) (*fleet.SetupExperienceInitResult, error) {
	// skipauth: No authorization check needed due to implementation returning
	// only license error.
	svc.authz.SkipAuthorization(ctx)

	return nil, fleet.ErrMissingLicense
}