diff --git a/lib/auth/windows/ldap.go b/lib/auth/windows/ldap.go
index 1e0984329a94c..9a7ce6738a8cb 100644
--- a/lib/auth/windows/ldap.go
+++ b/lib/auth/windows/ldap.go
@@ -18,6 +18,7 @@ package windows
 
 import (
 	"crypto/x509"
+	"errors"
 	"fmt"
 	"strings"
 	"sync"
@@ -164,6 +165,39 @@ func (c *LDAPClient) Close() {
 	c.mu.Unlock()
 }
 
+// convertLDAPError attempts to convert LDAP error codes to their
+// equivalent trace errors.
+func convertLDAPError(err error) error {
+	if err == nil {
+		return nil
+	}
+
+	var ldapErr *ldap.Error
+	if errors.As(err, &ldapErr) {
+		switch ldapErr.ResultCode {
+		case ldap.ErrorNetwork:
+			// this one is especially important, because Teleport will
+			// try to re-establish the connection when a ConnectionProblem
+			// is detected
+			return trace.ConnectionProblem(err, "network error")
+		case ldap.LDAPResultOperationsError:
+			if strings.Contains(err.Error(), "successful bind must be completed") {
+				return trace.AccessDenied(
+					"the LDAP server did not accept Teleport's client certificate, " +
+						"has the Teleport CA been imported correctly?")
+			}
+		case ldap.LDAPResultEntryAlreadyExists:
+			return trace.AlreadyExists("LDAP object already exists: %v", err)
+		case ldap.LDAPResultConstraintViolation:
+			return trace.BadParameter("object constraint violation: %v", err)
+		case ldap.LDAPResultInsufficientAccessRights:
+			return trace.AccessDenied("insufficient permissions: %v", err)
+		}
+	}
+
+	return err
+}
+
 // ReadWithFilter searches the specified DN (and its children) using the specified LDAP filter.
 // See https://ldap.com/ldap-filters/ for more information on LDAP filter syntax.
 func (c *LDAPClient) ReadWithFilter(dn string, filter string, attrs []string) ([]*ldap.Entry, error) {
@@ -180,12 +214,12 @@ func (c *LDAPClient) ReadWithFilter(dn string, filter string, attrs []string) ([
 	)
 	c.mu.Lock()
 	defer c.mu.Unlock()
+
 	res, err := c.client.SearchWithPaging(req, searchPageSize)
-	if ldap.IsErrorWithCode(err, ldap.ErrorNetwork) {
-		return nil, trace.ConnectionProblem(err, "fetching LDAP object %q with filter %q: %v", dn, filter, err)
-	} else if err != nil {
-		return nil, trace.Wrap(err, "fetching LDAP object %q with filter %q: %v", dn, filter, err)
+	if err != nil {
+		return nil, trace.Wrap(convertLDAPError(err), "fetching LDAP object %q with filter %q", dn, filter)
 	}
+
 	return res.Entries, nil
 }
 
@@ -220,19 +254,7 @@ func (c *LDAPClient) Create(dn string, class string, attrs map[string][]string)
 	defer c.mu.Unlock()
 
 	if err := c.client.Add(req); err != nil {
-		if ldapErr, ok := err.(*ldap.Error); ok {
-			switch ldapErr.ResultCode {
-			case ldap.LDAPResultEntryAlreadyExists:
-				return trace.AlreadyExists("LDAP object %q already exists: %v", dn, err)
-			case ldap.LDAPResultConstraintViolation:
-				return trace.BadParameter("object constraint violation on %q: %v", dn, err)
-			case ldap.LDAPResultInsufficientAccessRights:
-				return trace.AccessDenied("insufficient permissions to create %q: %v", dn, err)
-			case ldap.ErrorNetwork:
-				return trace.ConnectionProblem(err, "network error creating %q", dn)
-			}
-		}
-		return trace.Wrap(err, "error creating LDAP object %q: %v", dn, err)
+		return trace.Wrap(convertLDAPError(err), "error creating LDAP object %q", dn)
 	}
 	return nil
 }
@@ -244,9 +266,8 @@ func (c *LDAPClient) CreateContainer(dn string) error {
 	// Ignore the error if container already exists.
 	if trace.IsAlreadyExists(err) {
 		return nil
-	} else if ldap.IsErrorWithCode(err, ldap.ErrorNetwork) {
-		return trace.ConnectionProblem(err, "creating %v", dn)
 	}
+
 	return trace.Wrap(err)
 }
 
@@ -267,10 +288,8 @@ func (c *LDAPClient) Update(dn string, replaceAttrs map[string][]string) error {
 	c.mu.Lock()
 	defer c.mu.Unlock()
 
-	if err := c.client.Modify(req); ldap.IsErrorWithCode(err, ldap.ErrorNetwork) {
-		return trace.ConnectionProblem(err, "updating %q", dn)
-	} else if err != nil {
-		return trace.Wrap(err, "updating %q: %v", dn, err)
+	if err := c.client.Modify(req); err != nil {
+		return trace.Wrap(convertLDAPError(err), "updating %q", dn)
 	}
 	return nil
 }