diff --git a/internal/bridge/bridge.go b/internal/bridge/bridge.go
index a570d2de..7e1f6387 100644
--- a/internal/bridge/bridge.go
+++ b/internal/bridge/bridge.go
@@ -50,6 +50,7 @@ import (
 	"github.com/ProtonMail/proton-bridge/v3/internal/services/syncservice"
 	"github.com/ProtonMail/proton-bridge/v3/internal/telemetry"
 	"github.com/ProtonMail/proton-bridge/v3/internal/unleash"
+	"github.com/ProtonMail/proton-bridge/v3/internal/updater"
 	"github.com/ProtonMail/proton-bridge/v3/internal/user"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
 	"github.com/ProtonMail/proton-bridge/v3/pkg/keychain"
@@ -439,6 +440,15 @@ func (bridge *Bridge) init(tlsReporter TLSReporter) error {
 		version, err := bridge.updater.GetVersionInfo(ctx, bridge.api, bridge.vault.GetUpdateChannel())
 		if err != nil {
 			bridge.publish(events.UpdateCheckFailed{Error: err})
+			if errors.Is(err, updater.ErrVersionFileDownloadOrVerify) {
+				logPkg.WithError(err).Error("Cannot download or verify the version file")
+				if reporterErr := bridge.reporter.ReportMessageWithContext(
+					"Cannot download or verify the version file",
+					reporter.Context{"error": err},
+				); reporterErr != nil {
+					logPkg.WithError(reporterErr).Error("Failed to report version file check error")
+				}
+			}
 		} else {
 			bridge.handleUpdate(version)
 		}
diff --git a/internal/updater/updater.go b/internal/updater/updater.go
index 68d19ec6..14216c3e 100644
--- a/internal/updater/updater.go
+++ b/internal/updater/updater.go
@@ -32,9 +32,10 @@ import (
 )
 
 var (
-	ErrDownloadVerify         = errors.New("failed to download or verify the update")
-	ErrInstall                = errors.New("failed to install the update")
-	ErrUpdateAlreadyInstalled = errors.New("update is already installed")
+	ErrDownloadVerify              = errors.New("failed to download or verify the update")
+	ErrInstall                     = errors.New("failed to install the update")
+	ErrUpdateAlreadyInstalled      = errors.New("update is already installed")
+	ErrVersionFileDownloadOrVerify = errors.New("failed to download or verify the version file")
 )
 
 type Downloader interface {
@@ -72,7 +73,7 @@ func (u *Updater) GetVersionInfo(ctx context.Context, downloader Downloader, cha
 		u.getVersionFileURL()+".sig",
 	)
 	if err != nil {
-		return VersionInfo{}, err
+		return VersionInfo{}, fmt.Errorf("%w: %w", ErrVersionFileDownloadOrVerify, err)
 	}
 
 	var versionMap VersionMap