diff --git a/app/controlplane/internal/service/service.go b/app/controlplane/internal/service/service.go
index 386a0af63..5871b4ce6 100644
--- a/app/controlplane/internal/service/service.go
+++ b/app/controlplane/internal/service/service.go
@@ -543,6 +543,11 @@ func handleUseCaseErr(ctx context.Context, err error, l *log.Helper) error {
 		return status.Error(codes.AlreadyExists, err.Error())
 	case biz.IsErrReleasedVersionImmutable(err):
 		return status.Error(codes.FailedPrecondition, err.Error())
+	case biz.IsErrInvalidPassphrase(err):
+		// Client-side condition: the state was encrypted with a different token
+		// than the one used to resume the attestation. Surface it as a known
+		// error instead of masking it and reporting it to Sentry.
+		return status.Error(codes.FailedPrecondition, err.Error())
 	default:
 		// Client errors already converted by this function can be processed again
 		// (e.g. AttestationService.Store wraps storeAttestation, which converts internally).
diff --git a/app/controlplane/internal/service/service_test.go b/app/controlplane/internal/service/service_test.go
index 2bf2a8bae..40beba66d 100644
--- a/app/controlplane/internal/service/service_test.go
+++ b/app/controlplane/internal/service/service_test.go
@@ -133,6 +133,15 @@ func TestHandleUseCaseErr(t *testing.T) {
 			wantCode:    codes.NotFound,
 			wantMessage: "failed to find membership: organization chainloop not found",
 		},
+		{
+			// An attestation resumed with a different token cannot be decrypted.
+			// It is a client-side condition, so it must reach the user as a
+			// FailedPrecondition naming the cause instead of a masked 500.
+			name:        "invalid passphrase maps to failed precondition",
+			err:         fmt.Errorf("failed to decrypt attestation state: %w", biz.NewErrInvalidPassphrase()),
+			wantCode:    codes.FailedPrecondition,
+			wantMessage: "failed to decrypt attestation state: " + biz.NewErrInvalidPassphrase().Error(),
+		},
 	}
 
 	for _, tc := range testCases {
diff --git a/app/controlplane/pkg/biz/attestationstate.go b/app/controlplane/pkg/biz/attestationstate.go
index faa90dfce..af4da45a3 100644
--- a/app/controlplane/pkg/biz/attestationstate.go
+++ b/app/controlplane/pkg/biz/attestationstate.go
@@ -274,7 +274,9 @@ func decrypt(ciphertext []byte, passphrase string) ([]byte, error) {
 
 	// Check if the decrypted data starts with the magic string
 	if string(ciphertext[:len(magic)]) != magic {
-		return nil, fmt.Errorf("incorrect passphrase")
+		// A mismatch means the state was encrypted with a different passphrase,
+		// i.e. a different request token, not a server-side failure.
+		return nil, NewErrInvalidPassphrase()
 	}
 
 	return ciphertext[len(magic):], nil
diff --git a/app/controlplane/pkg/biz/attestationstate_integration_test.go b/app/controlplane/pkg/biz/attestationstate_integration_test.go
index d867d486a..bb52af53c 100644
--- a/app/controlplane/pkg/biz/attestationstate_integration_test.go
+++ b/app/controlplane/pkg/biz/attestationstate_integration_test.go
@@ -160,7 +160,8 @@ func (s *attestationStateTestSuite) TestRead() {
 		s.NoError(err)
 
 		got, err := s.AttestationState.Read(ctx, s.workflowOrg1.ID.String(), s.runOrg1.ID.String(), "wrong-passphrase")
-		s.ErrorContains(err, "incorrect passphrase")
+		s.ErrorContains(err, "created with a different token")
+		s.True(biz.IsErrInvalidPassphrase(err))
 		s.Nil(got)
 	})
 
@@ -173,7 +174,8 @@ func (s *attestationStateTestSuite) TestRead() {
 		s.NoError(err)
 
 		got, err := s.AttestationState.Read(ctx, s.workflowOrg1.ID.String(), s.runOrg1.ID.String(), s.passphrase)
-		s.ErrorContains(err, "incorrect passphrase")
+		s.ErrorContains(err, "created with a different token")
+		s.True(biz.IsErrInvalidPassphrase(err))
 		s.Nil(got)
 	})
 }
diff --git a/app/controlplane/pkg/biz/attestationstate_test.go b/app/controlplane/pkg/biz/attestationstate_test.go
new file mode 100644
index 000000000..bd243d29d
--- /dev/null
+++ b/app/controlplane/pkg/biz/attestationstate_test.go
@@ -0,0 +1,51 @@
+//
+// Copyright 2024-2026 The Chainloop Authors.
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package biz
+
+import (
+	"fmt"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestDecryptWrongPassphraseReturnsTypedError(t *testing.T) {
+	t.Parallel()
+
+	ciphertext, err := encrypt([]byte("hello attestation"), "correct-passphrase")
+	require.NoError(t, err)
+
+	// The passphrase that created the ciphertext still decrypts it.
+	plaintext, err := decrypt(ciphertext, "correct-passphrase")
+	require.NoError(t, err)
+	assert.Equal(t, []byte("hello attestation"), plaintext)
+
+	// A different passphrase is reported as a typed error so the service layer
+	// can turn it into a client error instead of masking it as a server error.
+	_, err = decrypt(ciphertext, "another-passphrase")
+	require.Error(t, err)
+	assert.True(t, IsErrInvalidPassphrase(err), "expected ErrInvalidPassphrase, got %T: %v", err, err)
+}
+
+// The read path wraps the decryption error with %w, so the typed error must
+// still be discoverable through errors.As.
+func TestErrInvalidPassphraseIsDiscoverableWhenWrapped(t *testing.T) {
+	t.Parallel()
+
+	wrapped := fmt.Errorf("failed to decrypt attestation state: %w", NewErrInvalidPassphrase())
+	assert.True(t, IsErrInvalidPassphrase(wrapped))
+}
diff --git a/app/controlplane/pkg/biz/errors.go b/app/controlplane/pkg/biz/errors.go
index 9216ce8ae..b6b2cdc54 100644
--- a/app/controlplane/pkg/biz/errors.go
+++ b/app/controlplane/pkg/biz/errors.go
@@ -200,3 +200,22 @@ func (e ErrAlreadyExists) Error() string {
 func IsErrAlreadyExists(err error) bool {
 	return errors.As(err, &ErrAlreadyExists{})
 }
+
+// ErrInvalidPassphrase is returned when the attestation state stored for a
+// workflow run cannot be decrypted with the passphrase derived from the current
+// request token. It typically means the state was created by a run that
+// authenticated with a different token, for example after the API token was
+// rotated.
+type ErrInvalidPassphrase struct{}
+
+func NewErrInvalidPassphrase() ErrInvalidPassphrase {
+	return ErrInvalidPassphrase{}
+}
+
+func (e ErrInvalidPassphrase) Error() string {
+	return "the attestation state was created with a different token, use the same token that ran 'attestation init', or reset the attestation and run 'attestation init' again"
+}
+
+func IsErrInvalidPassphrase(err error) bool {
+	return errors.As(err, &ErrInvalidPassphrase{})
+}