diff --git a/go.mod b/go.mod
index 097d4443..76f61de3 100644
--- a/go.mod
+++ b/go.mod
@@ -13,7 +13,7 @@ require (
 	github.com/pkg/errors v0.9.1
 	github.com/pkg/sftp v1.13.4
 	github.com/stretchr/testify v1.7.0
-	golang.org/x/crypto v0.0.0-20220307211146-efcb8507fb70
+	golang.org/x/crypto v0.40.0
 )
 
 require (
@@ -33,6 +33,6 @@ require (
 	github.com/aws/smithy-go v1.22.4 // indirect
 	github.com/davecgh/go-spew v1.1.0 // indirect
 	github.com/pmezard/go-difflib v1.0.0 // indirect
-	golang.org/x/sys v0.0.0-20210615035016-665e8c7367d1 // indirect
+	golang.org/x/sys v0.34.0 // indirect
 	gopkg.in/yaml.v3 v3.0.0-20200313102051-9f266ea9e77c // indirect
 )
diff --git a/go.sum b/go.sum
index da3fbfcb..0fc4037b 100644
--- a/go.sum
+++ b/go.sum
@@ -55,8 +55,8 @@ github.com/yuin/goldmark v1.3.5/go.mod h1:mwnBkeHKe2W/ZEtQ+71ViKU8L12m81fl3OWwC1
 golang.org/x/crypto v0.0.0-20190308221718-c2843e01d9a2/go.mod h1:djNgcEr1/C05ACkg1iLfiJU5Ep61QUkGW8qpdssI0+w=
 golang.org/x/crypto v0.0.0-20191011191535-87dc89f01550/go.mod h1:yigFU9vqHzYiE8UmvKecakEJjdnWj3jj499lnFckfCI=
 golang.org/x/crypto v0.0.0-20210421170649-83a5a9bb288b/go.mod h1:T9bdIzuCu7OtxOm1hfPfRQxPLYneinmdGuTeoZ9dtd4=
-golang.org/x/crypto v0.0.0-20220307211146-efcb8507fb70 h1:syTAU9FwmvzEoIYMqcPHOcVm4H3U5u90WsvuYgwpETU=
-golang.org/x/crypto v0.0.0-20220307211146-efcb8507fb70/go.mod h1:IxCIyHEi3zRg3s0A5j5BB6A9Jmi73HwBIUl50j+osU4=
+golang.org/x/crypto v0.40.0 h1:r4x+VvoG5Fm+eJcxMaY8CQM7Lb0l1lsmjGBQ6s8BfKM=
+golang.org/x/crypto v0.40.0/go.mod h1:Qr1vMER5WyS2dfPHAlsOj01wgLbsyWtFn/aY+5+ZdxY=
 golang.org/x/mod v0.4.2/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
 golang.org/x/net v0.0.0-20190404232315-eb5bcb51f2a3/go.mod h1:t9HGtf8HONx5eT2rtn7q6eTqICYqUVnKs3thJo3Qplg=
 golang.org/x/net v0.0.0-20190620200207-3b0461eec859/go.mod h1:z5CRVTTTmAJ677TzLLGU+0bjPO0LkuOLi4/5GtJWs/s=
@@ -70,10 +70,11 @@ golang.org/x/sys v0.0.0-20201119102817-f84b799fce68/go.mod h1:h1NjWce9XRLGQEsW7w
 golang.org/x/sys v0.0.0-20210330210617-4fbd30eecc44/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20210423185535-09eb48e85fd7/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20210510120138-977fb7262007/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
-golang.org/x/sys v0.0.0-20210615035016-665e8c7367d1 h1:SrN+KX8Art/Sf4HNj6Zcz06G7VEz+7w9tdXTPOZ7+l4=
-golang.org/x/sys v0.0.0-20210615035016-665e8c7367d1/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
-golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1 h1:v+OssWQX+hTHEmOBgwxdZxK4zHq3yOs8F9J7mk0PY8E=
+golang.org/x/sys v0.34.0 h1:H5Y5sJ2L2JRdyv7ROF1he/lPdvFsd0mJHFw2ThKHxLA=
+golang.org/x/sys v0.34.0/go.mod h1:BJP2sWEmIv4KK5OTEluFJCKSidICx8ciO85XgH3Ak8k=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
+golang.org/x/term v0.33.0 h1:NuFncQrRcaRvVmgRkvM3j/F00gWIAlcmlB8ACEKmGIg=
+golang.org/x/term v0.33.0/go.mod h1:s18+ql9tYWp1IfpV9DmCtQDDSRBUjKaw9M1eAv5UeF0=
 golang.org/x/text v0.3.0/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.3/go.mod h1:5Zoc/QRtKVWzQhOtBMvqHzDpF6irO9z98xDceosuGiQ=
 golang.org/x/tools v0.0.0-20180917221912-90fa682c2a6e/go.mod h1:n7NCudcB/nEzxVGmLbDWY5pfWTLqBcC2KZ6jyYvM4mQ=
diff --git a/managedserver.go b/managedserver.go
index 07d90917..02d40717 100644
--- a/managedserver.go
+++ b/managedserver.go
@@ -1,6 +1,7 @@
 package sftp
 
 import (
+	"errors"
 	"fmt"
 	"io"
 	"net"
@@ -28,6 +29,20 @@ type Alerter func(title string, metadata map[string]interface{})
 // is valid.
 type DriverGenerator func(LoginRequest) ServerDriver
 
+// DriverGeneratorWithError is a DriverGenerator that can explain a denial: returning a
+// nil driver with a *RejectionError sends the error's message to the SSH client.
+type DriverGeneratorWithError func(LoginRequest) (ServerDriver, error)
+
+// RejectionError rejects a login with a message shown to the SSH client as an
+// authentication banner (most clients print it before "Permission denied").
+type RejectionError struct {
+	Message string
+}
+
+func (e *RejectionError) Error() string {
+	return e.Message
+}
+
 // LoginRequest is the metadata associated with a login request that is passed to the
 // driverGenerator function in order for it to approve/deny the request.
 type LoginRequest struct {
@@ -43,7 +58,7 @@ type subsystemRequest struct {
 
 // ManagedServer is our term for the SFTP server.
 type ManagedServer struct {
-	driverGenerator func(LoginRequest) ServerDriver
+	driverGenerator DriverGeneratorWithError
 	lg              Logger
 	alertFn         Alerter
 }
@@ -51,6 +66,14 @@ type ManagedServer struct {
 // NewManagedServer creates a new ManagedServer which conditionally serves requests based
 // on the output of driverGenerator.
 func NewManagedServer(driverGenerator DriverGenerator, lg Logger, alertFn Alerter) *ManagedServer {
+	return NewManagedServerWithError(func(r LoginRequest) (ServerDriver, error) {
+		return driverGenerator(r), nil
+	}, lg, alertFn)
+}
+
+// NewManagedServerWithError is NewManagedServer for a DriverGeneratorWithError, allowing
+// denials to carry a client-visible message via *RejectionError.
+func NewManagedServerWithError(driverGenerator DriverGeneratorWithError, lg Logger, alertFn Alerter) *ManagedServer {
 	return &ManagedServer{
 		driverGenerator: driverGenerator,
 		lg:              lg,
@@ -58,6 +81,20 @@ func NewManagedServer(driverGenerator DriverGenerator, lg Logger, alertFn Alerte
 	}
 }
 
+// rejectionToSSHError converts a driver-generator denial into the error returned to the
+// ssh auth callback, sending a banner to the client when a *RejectionError is provided.
+func rejectionToSSHError(genErr error, username string) error {
+	var rejection *RejectionError
+	if errors.As(genErr, &rejection) {
+		message := rejection.Message
+		if !strings.HasSuffix(message, "\n") {
+			message += "\n"
+		}
+		return &ssh.BannerError{Err: genErr, Message: message}
+	}
+	return fmt.Errorf("password rejected for %q", username)
+}
+
 func (m ManagedServer) errorAndAlert(title string, metadata map[string]interface{}) {
 	if m.alertFn != nil {
 		m.alertFn(title, metadata)
@@ -109,26 +146,28 @@ func (m ManagedServer) Start(port int, rawPrivateKeys [][]byte, ciphers, macs []
 					MACs:    macs,
 				},
 				PasswordCallback: func(c ssh.ConnMetadata, pass []byte) (*ssh.Permissions, error) {
-					driver = m.driverGenerator(LoginRequest{
+					var genErr error
+					driver, genErr = m.driverGenerator(LoginRequest{
 						Username:   c.User(),
 						Password:   string(pass),
 						PublicKey:  "",
 						RemoteAddr: c.RemoteAddr(),
 					})
 					if driver == nil {
-						return nil, fmt.Errorf("password rejected for %q", c.User())
+						return nil, rejectionToSSHError(genErr, c.User())
 					}
 					return nil, nil
 				},
 				PublicKeyCallback: func(c ssh.ConnMetadata, key ssh.PublicKey) (*ssh.Permissions, error) {
-					driver = m.driverGenerator(LoginRequest{
+					var genErr error
+					driver, genErr = m.driverGenerator(LoginRequest{
 						Username:   c.User(),
 						Password:   "",
 						PublicKey:  strings.TrimSpace(string(ssh.MarshalAuthorizedKey(key))),
 						RemoteAddr: c.RemoteAddr(),
 					})
 					if driver == nil {
-						return nil, fmt.Errorf("password rejected for %q", c.User())
+						return nil, rejectionToSSHError(genErr, c.User())
 					}
 					return nil, nil
 				},
diff --git a/managedserver_test.go b/managedserver_test.go
new file mode 100644
index 00000000..1354aee2
--- /dev/null
+++ b/managedserver_test.go
@@ -0,0 +1,58 @@
+package sftp
+
+import (
+	"fmt"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"golang.org/x/crypto/ssh"
+)
+
+func TestRejectionToSSHError(t *testing.T) {
+	for _, spec := range []struct {
+		desc           string
+		genErr         error
+		wantBanner     string
+		wantGenericMsg bool
+	}{
+		{
+			desc:       "rejection error becomes banner with trailing newline",
+			genErr:     &RejectionError{Message: "use sftp2.clever.com"},
+			wantBanner: "use sftp2.clever.com\n",
+		},
+		{
+			desc:       "rejection error keeps existing trailing newline",
+			genErr:     &RejectionError{Message: "use sftp2.clever.com\n"},
+			wantBanner: "use sftp2.clever.com\n",
+		},
+		{
+			desc:       "wrapped rejection error becomes banner",
+			genErr:     fmt.Errorf("login denied: %w", &RejectionError{Message: "use sftp2.clever.com"}),
+			wantBanner: "use sftp2.clever.com\n",
+		},
+		{
+			desc:           "nil error yields generic rejection",
+			genErr:         nil,
+			wantGenericMsg: true,
+		},
+		{
+			desc:           "plain error yields generic rejection",
+			genErr:         fmt.Errorf("some internal failure"),
+			wantGenericMsg: true,
+		},
+	} {
+		t.Run(spec.desc, func(t *testing.T) {
+			err := rejectionToSSHError(spec.genErr, "some-user")
+			assert.Error(t, err)
+
+			if spec.wantGenericMsg {
+				assert.Equal(t, `password rejected for "some-user"`, err.Error())
+				return
+			}
+
+			bannerErr, ok := err.(*ssh.BannerError)
+			assert.True(t, ok, "expected *ssh.BannerError, got %T", err)
+			assert.Equal(t, spec.wantBanner, bannerErr.Message)
+		})
+	}
+}