diff --git a/pkg/api/ldap_debug.go b/pkg/api/ldap_debug.go
index b9064e9bb20..44e194e8d6b 100644
--- a/pkg/api/ldap_debug.go
+++ b/pkg/api/ldap_debug.go
@@ -1,7 +1,6 @@
 package api
 
 import (
-	"context"
 	"fmt"
 	"net/http"
 
@@ -18,7 +17,6 @@ import (
 var (
 	getLDAPConfig = multildap.GetConfig
 	newLDAP       = multildap.New
-	tokenService  = AuthToken{}.TokenService
 
 	logger = log.New("LDAP.debug")
 
@@ -61,14 +59,6 @@ type LDAPServerDTO struct {
 	Error     string `json:"error"`
 }
 
-type AuthToken struct {
-	TokenService TokenRevoker `inject:""`
-}
-
-type TokenRevoker interface {
-	RevokeAllUserTokens(context.Context, int64) error
-}
-
 // FetchOrgs fetches the organization(s) information by executing a single query to the database. Then, populating the DTO with the information retrieved.
 func (user *LDAPUserDTO) FetchOrgs() error {
 	orgIds := []int64{}
@@ -199,8 +189,7 @@ func (server *HTTPServer) PostSyncUserWithLDAP(c *models.ReqContext) Response {
 	user, _, err := ldapServer.User(query.Result.Login)
 
 	if err != nil {
-		if err == ldap.ErrCouldNotFindUser { // User was not in the LDAP server - we need to take action:
-
+		if err == multildap.ErrDidNotFindUser { // User was not in the LDAP server - we need to take action:
 			if setting.AdminUser == query.Result.Login { // User is *the* Grafana Admin. We cannot disable it.
 				errMsg := fmt.Sprintf(`Refusing to sync grafana super admin "%s" - it would be disabled`, query.Result.Login)
 				logger.Error(errMsg)
@@ -214,13 +203,16 @@ func (server *HTTPServer) PostSyncUserWithLDAP(c *models.ReqContext) Response {
 				return Error(http.StatusInternalServerError, "Failed to disable the user", err)
 			}
 
-			err = tokenService.RevokeAllUserTokens(context.TODO(), userId)
+			err = server.AuthTokenService.RevokeAllUserTokens(c.Req.Context(), userId)
 			if err != nil {
 				return Error(http.StatusInternalServerError, "Failed to remove session tokens for the user", err)
 			}
 
-			return Success("User disabled without any updates in the information") // should this be a success?
+			return Error(http.StatusBadRequest, "User not found in LDAP. Disabled the user without updating information", nil) // should this be a success?
 		}
+
+		logger.Debug("Failed to sync the user with LDAP", "err", err)
+		return Error(http.StatusBadRequest, "Something went wrong while finding the user in LDAP", err)
 	}
 
 	upsertCmd := &models.UpsertUserCommand{
diff --git a/pkg/api/ldap_debug_test.go b/pkg/api/ldap_debug_test.go
index ce930b455e7..e065a8f6091 100644
--- a/pkg/api/ldap_debug_test.go
+++ b/pkg/api/ldap_debug_test.go
@@ -1,7 +1,6 @@
 package api
 
 import (
-	"context"
 	"errors"
 	"net/http"
 	"net/http/httptest"
@@ -9,6 +8,7 @@ import (
 
 	"github.com/grafana/grafana/pkg/bus"
 	"github.com/grafana/grafana/pkg/models"
+	"github.com/grafana/grafana/pkg/services/auth"
 	"github.com/grafana/grafana/pkg/services/ldap"
 	"github.com/grafana/grafana/pkg/services/multildap"
 	"github.com/grafana/grafana/pkg/setting"
@@ -20,9 +20,6 @@ type LDAPMock struct {
 	Results []*models.ExternalUserInfo
 }
 
-type TokenServiceMock struct {
-}
-
 var userSearchResult *models.ExternalUserInfo
 var userSearchConfig ldap.ServerConfig
 var userSearchError error
@@ -46,10 +43,6 @@ func (m *LDAPMock) User(login string) (*models.ExternalUserInfo, ldap.ServerConf
 	return userSearchResult, userSearchConfig, userSearchError
 }
 
-func (ts *TokenServiceMock) RevokeAllUserTokens(ctx context.Context, userId int64) error {
-	return nil
-}
-
 //***
 // GetUserFromLDAP tests
 //***
@@ -391,7 +384,7 @@ func postSyncUserWithLDAPContext(t *testing.T, requestURL string) *scenarioConte
 	setting.LDAPEnabled = true
 	defer func() { setting.LDAPEnabled = ldap }()
 
-	hs := &HTTPServer{Cfg: setting.NewCfg()}
+	hs := &HTTPServer{Cfg: setting.NewCfg(), AuthTokenService: auth.NewFakeUserAuthTokenService()}
 
 	sc.defaultHandler = Wrap(func(c *models.ReqContext) Response {
 		sc.context = c
@@ -490,7 +483,7 @@ func TestPostSyncUserWithLDAPAPIEndpoint_WhenGrafanaAdmin(t *testing.T) {
 		return &LDAPMock{}
 	}
 
-	userSearchError = ldap.ErrCouldNotFindUser
+	userSearchError = multildap.ErrDidNotFindUser
 
 	admin := setting.AdminUser
 	setting.AdminUser = "ldap-daniel"
@@ -516,7 +509,7 @@ func TestPostSyncUserWithLDAPAPIEndpoint_WhenGrafanaAdmin(t *testing.T) {
 
 	expected := `
 	{
-		"error": "Can't find user in LDAP",
+		"error": "Did not find a user",
 		"message": "Refusing to sync grafana super admin \"ldap-daniel\" - it would be disabled"
 	}
 	`
@@ -529,8 +522,6 @@ func TestPostSyncUserWithLDAPAPIEndpoint_WhenUserNotInLDAP(t *testing.T) {
 		return &ldap.Config{}, nil
 	}
 
-	tokenService = &TokenServiceMock{}
-
 	newLDAP = func(_ []*ldap.ServerConfig) multildap.IMultiLDAP {
 		return &LDAPMock{}
 	}
@@ -563,11 +554,11 @@ func TestPostSyncUserWithLDAPAPIEndpoint_WhenUserNotInLDAP(t *testing.T) {
 
 	sc := postSyncUserWithLDAPContext(t, "/api/admin/ldap/sync/34")
 
-	assert.Equal(t, http.StatusOK, sc.resp.Code)
+	assert.Equal(t, http.StatusBadRequest, sc.resp.Code)
 
 	expected := `
 	{
-		"message": "User disabled without any updates in the information"
+		"message": "User not found in LDAP. Disabled the user without updating information"
 	}
 	`
 
diff --git a/public/app/features/admin/UserSyncInfo.tsx b/public/app/features/admin/UserSyncInfo.tsx
index 577014d0392..33be5683751 100644
--- a/public/app/features/admin/UserSyncInfo.tsx
+++ b/public/app/features/admin/UserSyncInfo.tsx
@@ -3,6 +3,7 @@ import { dateTime } from '@grafana/data';
 import { LdapUserSyncInfo } from 'app/types';
 
 interface Props {
+  disableSync: boolean;
   syncInfo: LdapUserSyncInfo;
   onSync?: () => void;
 }
@@ -31,21 +32,23 @@ export class UserSyncInfo extends PureComponent<Props, State> {
   };
 
   render() {
-    const { syncInfo } = this.props;
+    const { syncInfo, disableSync } = this.props;
     const { isSyncing } = this.state;
     const nextSyncTime = syncInfo.nextSync ? dateTime(syncInfo.nextSync).format(syncTimeFormat) : '';
     const prevSyncSuccessful = syncInfo && syncInfo.prevSync;
     const prevSyncTime = prevSyncSuccessful ? dateTime(syncInfo.prevSync).format(syncTimeFormat) : '';
+    const isDisabled = isSyncing || disableSync;
 
     return (
       <>
-        <h3 className="page-heading">
-          LDAP
-          <button className={`btn btn-secondary pull-right`} onClick={this.handleSyncClick} hidden={true}>
-            <span className="btn-title">Sync user</span>
-            {isSyncing && <i className="fa fa-spinner fa-fw fa-spin run-icon" />}
-          </button>
-        </h3>
+        <button className={`btn btn-secondary pull-right`} onClick={this.handleSyncClick} disabled={isDisabled}>
+          <span className="btn-title">Sync user</span>
+          {isSyncing && <i className="fa fa-spinner fa-fw fa-spin run-icon" />}
+        </button>
+
+        <div className="clearfix" />
+
+        <h3 className="page-heading">LDAP</h3>
         <div className="gf-form-group">
           <div className="gf-form">
             <table className="filter-table form-inline">
diff --git a/public/app/features/admin/ldap/LdapUserPage.tsx b/public/app/features/admin/ldap/LdapUserPage.tsx
index 582518158e6..c0fcff5f45b 100644
--- a/public/app/features/admin/ldap/LdapUserPage.tsx
+++ b/public/app/features/admin/ldap/LdapUserPage.tsx
@@ -86,6 +86,10 @@ export class LdapUserPage extends PureComponent<Props, State> {
     revokeAllSessions(userId);
   };
 
+  isUserError = (): boolean => {
+    return !!(this.props.userError && this.props.userError.title);
+  };
+
   render() {
     const { user, ldapUser, userError, navModel, sessions, ldapSyncInfo } = this.props;
     const { isLoading } = this.state;
@@ -102,7 +106,7 @@ export class LdapUserPage extends PureComponent<Props, State> {
       <Page navModel={navModel}>
         <Page.Contents isLoading={isLoading}>
           <div className="grafana-info-box">
-            This user is synced via LDAP – all changes must be done in LDAP or mappings.
+            This user is synced via LDAP – All changes must be done in LDAP or mappings.
           </div>
           {userError && userError.title && (
             <div className="gf-form-group">
@@ -115,9 +119,12 @@ export class LdapUserPage extends PureComponent<Props, State> {
             </div>
           )}
 
+          {userSyncInfo && (
+            <UserSyncInfo syncInfo={userSyncInfo} onSync={this.onSyncUser} disableSync={this.isUserError()} />
+          )}
+
           {ldapUser && <LdapUserInfo ldapUser={ldapUser} />}
           {!ldapUser && user && <UserInfo user={user} />}
-          {userSyncInfo && <UserSyncInfo syncInfo={userSyncInfo} onSync={this.onSyncUser} />}
 
           {sessions && (
             <UserSessions