diff --git a/go.mod b/go.mod
index 3b4bf9da7..6b19b7fbc 100644
--- a/go.mod
+++ b/go.mod
@@ -346,7 +346,7 @@ require (
 	github.com/davecgh/go-spew v1.1.2-0.20180830191138-d8f796af33cc // indirect
 	github.com/desertbit/timer v0.0.0-20180107155436-c41aec40b27f // indirect
 	github.com/digitorus/pkcs7 v0.0.0-20230818184609-3a137a874352 // indirect
-	github.com/digitorus/timestamp v0.0.0-20231217203849-220c5c2851b7
+	github.com/digitorus/timestamp v0.0.0-20231217203849-220c5c2851b7 // indirect
 	github.com/docker/cli v29.2.0+incompatible // indirect
 	github.com/docker/docker v28.5.2+incompatible // indirect
 	github.com/docker/docker-credential-helpers v0.9.4 // indirect
diff --git a/pkg/attestation/verifier/testdata/bundle_with_bad_timestamp.json b/pkg/attestation/verifier/testdata/bundle_with_bad_timestamp.json
new file mode 100644
index 000000000..01ac342c1
--- /dev/null
+++ b/pkg/attestation/verifier/testdata/bundle_with_bad_timestamp.json
@@ -0,0 +1,21 @@
+{
+   "mediaType": "application/vnd.dev.sigstore.bundle+json;version=0.3",
+   "verificationMaterial": {
+      "timestampVerificationData": {
+         "rfc3161Timestamps": [
+            {
+               "signedTimestamp": "bm90LWEtdmFsaWQtdHNy"
+            }
+         ]
+      }
+   },
+   "dsseEnvelope": {
+      "payload": "eyJfdHlwZSI6Imh0dHBzOi8vaW4tdG90by5pby9TdGF0ZW1lbnQvdjEifQ==",
+      "payloadType": "application/vnd.in-toto+json",
+      "signatures": [
+         {
+            "sig": "TUVVQ0lRQ1JjOFVmeFVSMnBkL2UxVW1pVmhkRE5BZUxVRi83ODZ2WGxCT1VWM0dJcUFJZ0NqOTROczZwbzFQSzJjTW95MzBpOVB3Smx5c1E0R1RmTGI4TnZ5WlB1ckk9"
+         }
+      ]
+   }
+}
diff --git a/pkg/attestation/verifier/testdata/dsse_envelope.json b/pkg/attestation/verifier/testdata/dsse_envelope.json
new file mode 100644
index 000000000..5be18f270
--- /dev/null
+++ b/pkg/attestation/verifier/testdata/dsse_envelope.json
@@ -0,0 +1,10 @@
+{
+  "payloadType": "application/vnd.in-toto+json",
+  "payload": "eyJfdHlwZSI6Imh0dHBzOi8vaW4tdG90by5pby9TdGF0ZW1lbnQvdjEifQ==",
+  "signatures": [
+    {
+      "keyid": "",
+      "sig": "MEUCIQDtest"
+    }
+  ]
+}
diff --git a/pkg/attestation/verifier/timestamp.go b/pkg/attestation/verifier/timestamp.go
index bb3f30050..a3b4ff327 100644
--- a/pkg/attestation/verifier/timestamp.go
+++ b/pkg/attestation/verifier/timestamp.go
@@ -1,5 +1,5 @@
 //
-// Copyright 2025 The Chainloop Authors.
+// Copyright 2025-2026 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.
@@ -22,24 +22,45 @@ import (
 	"errors"
 	"fmt"
 
-	"github.com/digitorus/timestamp"
 	"github.com/sigstore/sigstore-go/pkg/bundle"
+	"github.com/sigstore/sigstore-go/pkg/verify"
 	"github.com/sigstore/timestamp-authority/v2/pkg/verification"
 )
 
+var (
+	// ErrTSAResponseInvalid indicates the RFC3161 timestamp response could not
+	// be verified against the TSA certificate chain.
+	ErrTSAResponseInvalid = errors.New("TSA response verification failed")
+
+	// ErrTimestampOutsideTSAValidity indicates the timestamp's time falls
+	// outside the TSA certificate's NotBefore/NotAfter window.
+	ErrTimestampOutsideTSAValidity = errors.New("timestamp outside TSA certificate validity window")
+
+	// ErrSigningCertNotValidAtTimestamp indicates the signing certificate
+	// was not valid at the timestamp's time.
+	ErrSigningCertNotValidAtTimestamp = errors.New("signing certificate not valid at timestamp time")
+
+	// ErrNoTSARootsConfigured indicates the bundle contains signed timestamps
+	// but no TSA trust roots are configured on the server.
+	ErrNoTSARootsConfigured = errors.New("no TSA trust roots configured")
+)
+
 func VerifyTimestamps(sb *bundle.Bundle, tr *TrustedRoot) error {
 	signedTimestamps, err := sb.Timestamps()
 	if err != nil {
 		if errors.Is(err, bundle.ErrMissingVerificationMaterial) {
-			// translate error
 			return ErrMissingVerificationMaterial
 		}
 		return fmt.Errorf("could not get timestamps: %w", err)
 	}
 	if len(signedTimestamps) == 0 {
-		// nothing to do
 		return ErrMissingVerificationMaterial
 	}
+
+	if len(tr.TimestampAuthorities) == 0 {
+		return ErrNoTSARootsConfigured
+	}
+
 	sc, err := sb.SignatureContent()
 	if err != nil {
 		return fmt.Errorf("could not get signature material: %w", err)
@@ -53,48 +74,58 @@ func VerifyTimestamps(sb *bundle.Bundle, tr *TrustedRoot) error {
 	dst := make([]byte, base64.RawURLEncoding.DecodedLen(len(signature)))
 	i, err := base64.StdEncoding.Decode(dst, signature)
 	if err == nil {
-		// get the decoded one
 		sigBytes = dst[:i]
 	}
 
-	var verifiedTimestamps []*timestamp.Timestamp
+	vc, vcErr := sb.VerificationContent()
+	if vcErr != nil && !errors.Is(vcErr, bundle.ErrMissingVerificationMaterial) {
+		return fmt.Errorf("could not get verification material: %w", vcErr)
+	}
+
 	for _, st := range signedTimestamps {
-		// let's try with all TSAs
-		for _, tsa := range tr.TimestampAuthorities {
-			tsaCert := tsa[0]
-			var roots []*x509.Certificate
-			var intermediates []*x509.Certificate
-			if len(tsa) > 1 {
-				roots = tsa[len(tsa)-1:]
-				intermediates = tsa[1 : len(tsa)-1]
-			}
-			ts, err := verification.VerifyTimestampResponse(st, bytes.NewReader(sigBytes),
-				verification.VerifyOpts{
-					TSACertificate: tsaCert,
-					Intermediates:  intermediates,
-					Roots:          roots,
-				})
-			if err != nil {
-				continue
-			}
-			// verify timestamp time
-			if ts.Time.After(tsaCert.NotAfter) || ts.Time.Before(tsaCert.NotBefore) {
-				continue
-			}
-
-			vc, err := sb.VerificationContent()
-			if err != nil && !errors.Is(err, bundle.ErrMissingVerificationMaterial) {
-				return fmt.Errorf("could not get verification material: %w", err)
-			}
-			// verify signing certificate issuing time
-			if vc != nil && vc.Certificate() != nil && !vc.ValidAtTime(ts.Time, nil) {
-				continue
-			}
-			verifiedTimestamps = append(verifiedTimestamps, ts)
+		if err := verifyTimestamp(st, sigBytes, vc, tr); err != nil {
+			return err
 		}
 	}
-	if len(verifiedTimestamps) < len(signedTimestamps) {
-		return fmt.Errorf("some timestamps verification failed")
-	}
 	return nil
 }
+
+// verifyTimestamp tries to verify a single signed timestamp against every
+// configured TSA. Returns the error from the last attempted TSA on failure.
+func verifyTimestamp(st []byte, sigBytes []byte, vc verify.VerificationContent, tr *TrustedRoot) error {
+	var lastErr error
+	for _, tsa := range tr.TimestampAuthorities {
+		tsaCert := tsa[0]
+		var roots []*x509.Certificate
+		var intermediates []*x509.Certificate
+		if len(tsa) > 1 {
+			roots = tsa[len(tsa)-1:]
+			intermediates = tsa[1 : len(tsa)-1]
+		}
+
+		ts, err := verification.VerifyTimestampResponse(st, bytes.NewReader(sigBytes),
+			verification.VerifyOpts{
+				TSACertificate: tsaCert,
+				Intermediates:  intermediates,
+				Roots:          roots,
+			})
+		if err != nil {
+			lastErr = fmt.Errorf("%w: %w", ErrTSAResponseInvalid, err)
+			continue
+		}
+
+		if ts.Time.After(tsaCert.NotAfter) || ts.Time.Before(tsaCert.NotBefore) {
+			lastErr = fmt.Errorf("%w: timestamp=%s, cert validity=[%s, %s]",
+				ErrTimestampOutsideTSAValidity, ts.Time, tsaCert.NotBefore, tsaCert.NotAfter)
+			continue
+		}
+
+		if vc != nil && vc.Certificate() != nil && !vc.ValidAtTime(ts.Time, nil) {
+			lastErr = fmt.Errorf("%w: timestamp=%s", ErrSigningCertNotValidAtTimestamp, ts.Time)
+			continue
+		}
+
+		return nil
+	}
+	return lastErr
+}
diff --git a/pkg/attestation/verifier/verifier_test.go b/pkg/attestation/verifier/verifier_test.go
index b9eb647e7..a2e795bef 100644
--- a/pkg/attestation/verifier/verifier_test.go
+++ b/pkg/attestation/verifier/verifier_test.go
@@ -1,5 +1,5 @@
 //
-// Copyright 2025 The Chainloop Authors.
+// Copyright 2025-2026 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.
@@ -19,6 +19,7 @@ import (
 	"bytes"
 	"context"
 	"crypto/x509"
+	"errors"
 	"os"
 	"testing"
 
@@ -64,6 +65,12 @@ func TestVerifyBundle(t *testing.T) {
 			bundle:    "testdata/bundle_invalid.json",
 			expectErr: "validating the DSSE envelope",
 		},
+		{
+			name:      "legacy DSSE envelope (not a bundle)",
+			roots:     roots,
+			bundle:    "testdata/dsse_envelope.json",
+			expectErr: "invalid bundle",
+		},
 	}
 
 	for _, tc := range cases {
@@ -80,3 +87,43 @@ func TestVerifyBundle(t *testing.T) {
 		})
 	}
 }
+
+func TestVerifyTimestamps_TypedErrors(t *testing.T) {
+	ca, err := os.ReadFile("testdata/ca.pub")
+	require.NoError(t, err)
+	certs, err := cryptoutils.LoadCertificatesFromPEM(bytes.NewReader(ca))
+	require.NoError(t, err)
+
+	cases := []struct {
+		name           string
+		roots          *TrustedRoot
+		expectSentinel error
+	}{
+		{
+			name: "bad timestamp with TSA configured",
+			roots: &TrustedRoot{
+				TimestampAuthorities: map[string][]*x509.Certificate{
+					"fake-tsa": certs,
+				},
+			},
+			expectSentinel: ErrTSAResponseInvalid,
+		},
+		{
+			name:           "timestamp with no TSA roots configured",
+			roots:          &TrustedRoot{},
+			expectSentinel: ErrNoTSARootsConfigured,
+		},
+	}
+
+	bundleBytes, err := os.ReadFile("testdata/bundle_with_bad_timestamp.json")
+	require.NoError(t, err)
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			err := VerifyBundle(context.TODO(), bundleBytes, tc.roots)
+			require.Error(t, err)
+			assert.True(t, errors.Is(err, tc.expectSentinel),
+				"expected %v, got: %v", tc.expectSentinel, err)
+		})
+	}
+}