diff --git a/outpost/pkg/ldap/api.go b/outpost/pkg/ldap/api.go
index 473958952..d6b6f1657 100644
--- a/outpost/pkg/ldap/api.go
+++ b/outpost/pkg/ldap/api.go
@@ -3,7 +3,9 @@ package ldap
 import (
 	"errors"
 	"fmt"
+	"net/http"
 	"strings"
+	"sync"
 
 	"github.com/go-openapi/strfmt"
 	log "github.com/sirupsen/logrus"
@@ -29,6 +31,8 @@ func (ls *LDAPServer) Refresh() error {
 			appSlug:             *provider.ApplicationSlug,
 			flowSlug:            *provider.BindFlowSlug,
 			searchAllowedGroups: []*strfmt.UUID{provider.SearchGroup},
+			boundUsersMutex:     sync.RWMutex{},
+			boundUsers:          make(map[string]UserFlags),
 			s:                   ls,
 			log:                 log.WithField("logger", "authentik.outpost.ldap").WithField("provider", provider.Name),
 		}
@@ -48,3 +52,17 @@ func (ls *LDAPServer) Start() error {
 	}
 	return nil
 }
+
+type transport struct {
+	headers map[string]string
+}
+
+func (t *transport) RoundTrip(req *http.Request) (*http.Response, error) {
+	for key, value := range t.headers {
+		req.Header.Add(key, value)
+	}
+	return http.DefaultTransport.RoundTrip(req)
+}
+func newTransport(headers map[string]string) *transport {
+	return &transport{headers}
+}
diff --git a/outpost/pkg/ldap/instance_bind.go b/outpost/pkg/ldap/instance_bind.go
index 905f3060c..e9cb527f0 100644
--- a/outpost/pkg/ldap/instance_bind.go
+++ b/outpost/pkg/ldap/instance_bind.go
@@ -7,6 +7,7 @@ import (
 	"net"
 	"net/http"
 	"net/http/cookiejar"
+	"net/url"
 	"strings"
 	"time"
 
@@ -52,10 +53,21 @@ func (pi *ProviderInstance) Bind(username string, bindPW string, conn net.Conn)
 		pi.log.WithError(err).Warning("Failed to create cookiejar")
 		return ldap.LDAPResultOperationsError, nil
 	}
+	host, _, err := net.SplitHostPort(conn.RemoteAddr().String())
+	if err != nil {
+		pi.log.WithError(err).Warning("Failed to get remote IP")
+		return ldap.LDAPResultOperationsError, nil
+	}
+	// Create new http client that also sets the correct ip
 	client := &http.Client{
 		Jar: jar,
+		Transport: newTransport(map[string]string{
+			"X-authentik-remote-ip": host,
+		}),
 	}
-	passed, err := pi.solveFlowChallenge(username, bindPW, client)
+	params := url.Values{}
+	params.Add("goauthentik.io/outpost/ldap", "true")
+	passed, err := pi.solveFlowChallenge(username, bindPW, client, params.Encode())
 	if err != nil {
 		pi.log.WithField("boundDN", username).WithError(err).Warning("failed to solve challenge")
 		return ldap.LDAPResultOperationsError, nil
@@ -91,7 +103,7 @@ func (pi *ProviderInstance) Bind(username string, bindPW string, conn net.Conn)
 		UserInfo:  userInfo.Payload.User,
 		CanSearch: pi.SearchAccessCheck(userInfo.Payload.User),
 	}
-	pi.boundUsersMutex.Unlock()
+	defer pi.boundUsersMutex.Unlock()
 	pi.delayDeleteUserInfo(username)
 	return ldap.LDAPResultSuccess, nil
 }
@@ -127,13 +139,13 @@ func (pi *ProviderInstance) delayDeleteUserInfo(dn string) {
 	}()
 }
 
-func (pi *ProviderInstance) solveFlowChallenge(bindDN string, password string, client *http.Client) (bool, error) {
+func (pi *ProviderInstance) solveFlowChallenge(bindDN string, password string, client *http.Client, urlParams string) (bool, error) {
 	challenge, err := pi.s.ac.Client.Flows.FlowsExecutorGet(&flows.FlowsExecutorGetParams{
 		FlowSlug:   pi.flowSlug,
-		Query:      "ldap=true",
+		Query:      urlParams,
 		Context:    context.Background(),
 		HTTPClient: client,
-	}, httptransport.PassThroughAuth)
+	}, pi.s.ac.Auth)
 	if err != nil {
 		pi.log.WithError(err).Warning("Failed to get challenge")
 		return false, err
@@ -141,7 +153,7 @@ func (pi *ProviderInstance) solveFlowChallenge(bindDN string, password string, c
 	pi.log.WithField("component", challenge.Payload.Component).WithField("type", *challenge.Payload.Type).Debug("Got challenge")
 	responseParams := &flows.FlowsExecutorSolveParams{
 		FlowSlug:   pi.flowSlug,
-		Query:      "ldap=true",
+		Query:      urlParams,
 		Context:    context.Background(),
 		HTTPClient: client,
 	}
@@ -155,7 +167,7 @@ func (pi *ProviderInstance) solveFlowChallenge(bindDN string, password string, c
 	default:
 		return false, fmt.Errorf("unsupported challenge type: %s", challenge.Payload.Component)
 	}
-	response, err := pi.s.ac.Client.Flows.FlowsExecutorSolve(responseParams, httptransport.PassThroughAuth)
+	response, err := pi.s.ac.Client.Flows.FlowsExecutorSolve(responseParams, pi.s.ac.Auth)
 	pi.log.WithField("component", response.Payload.Component).WithField("type", *response.Payload.Type).Debug("Got response")
 	if *response.Payload.Type == "redirect" {
 		return true, nil
@@ -172,5 +184,5 @@ func (pi *ProviderInstance) solveFlowChallenge(bindDN string, password string, c
 			}
 		}
 	}
-	return pi.solveFlowChallenge(bindDN, password, client)
+	return pi.solveFlowChallenge(bindDN, password, client, urlParams)
 }
diff --git a/outpost/pkg/ldap/instance_search.go b/outpost/pkg/ldap/instance_search.go
index 4e5665adc..b7102c347 100644
--- a/outpost/pkg/ldap/instance_search.go
+++ b/outpost/pkg/ldap/instance_search.go
@@ -30,10 +30,10 @@ func (pi *ProviderInstance) Search(bindDN string, searchReq ldap.SearchRequest,
 	defer pi.boundUsersMutex.RUnlock()
 	flags, ok := pi.boundUsers[bindDN]
 	if !ok {
-		return ldap.ServerSearchResult{ResultCode: ldap.LDAPResultInsufficientAccessRights}, errors.New("Access denied")
+		return ldap.ServerSearchResult{ResultCode: ldap.LDAPResultInsufficientAccessRights}, errors.New("access denied")
 	}
 	if !flags.CanSearch {
-		return ldap.ServerSearchResult{ResultCode: ldap.LDAPResultInsufficientAccessRights}, errors.New("Access denied")
+		return ldap.ServerSearchResult{ResultCode: ldap.LDAPResultInsufficientAccessRights}, errors.New("access denied")
 	}
 
 	switch filterEntity {