diff --git a/cmd/oras/internal/display/status/deprecated.go b/cmd/oras/internal/display/status/deprecated.go
index f53875295..8fec00c32 100644
--- a/cmd/oras/internal/display/status/deprecated.go
+++ b/cmd/oras/internal/display/status/deprecated.go
@@ -58,7 +58,8 @@ var printer = NewPrinter(os.Stdout)
 
 // Print objects to display concurrent-safely.
 func Print(a ...any) error {
-	return printer.Println(a...)
+	printer.Println(a...)
+	return printer.errored
 }
 
 // StatusPrinter returns a tracking function for transfer status.
diff --git a/cmd/oras/internal/display/status/print.go b/cmd/oras/internal/display/status/print.go
index b2094964a..46410c915 100644
--- a/cmd/oras/internal/display/status/print.go
+++ b/cmd/oras/internal/display/status/print.go
@@ -20,6 +20,7 @@ import (
 	"fmt"
 	"io"
 	"oras.land/oras/internal/descriptor"
+	"os"
 	"sync"
 
 	ocispec "github.com/opencontainers/image-spec/specs-go/v1"
@@ -31,8 +32,9 @@ type PrintFunc func(ocispec.Descriptor) error
 
 // Printer prints for status handlers.
 type Printer struct {
-	out  io.Writer
-	lock sync.Mutex
+	out     io.Writer
+	lock    sync.Mutex
+	errored error
 }
 
 // NewPrinter creates a new Printer.
@@ -41,11 +43,18 @@ func NewPrinter(out io.Writer) *Printer {
 }
 
 // Println prints objects concurrent-safely with newline.
-func (p *Printer) Println(a ...any) error {
+func (p *Printer) Println(a ...any) {
 	p.lock.Lock()
 	defer p.lock.Unlock()
 	_, err := fmt.Fprintln(p.out, a...)
-	return err
+	if err != nil {
+		if p.errored == nil {
+			p.errored = fmt.Errorf("display output error: %w", err)
+			_, _ = fmt.Fprint(os.Stderr, p.errored)
+			return
+		}
+	}
+	return
 }
 
 // PrintStatus prints transfer status.
@@ -58,7 +67,8 @@ func (p *Printer) PrintStatus(desc ocispec.Descriptor, status string, verbose bo
 		}
 		name = desc.MediaType
 	}
-	return p.Println(status, descriptor.ShortDigest(desc), name)
+	p.Println(status, descriptor.ShortDigest(desc), name)
+	return p.errored
 }
 
 // StatusPrinter returns a tracking function for transfer status.
diff --git a/cmd/oras/internal/display/status/text.go b/cmd/oras/internal/display/status/text.go
index 56aa886b9..cd7924b44 100644
--- a/cmd/oras/internal/display/status/text.go
+++ b/cmd/oras/internal/display/status/text.go
@@ -44,12 +44,14 @@ func (ph *TextPushHandler) OnFileLoading(name string) error {
 	if !ph.verbose {
 		return nil
 	}
-	return ph.printer.Println("Preparing", name)
+	ph.printer.Println("Preparing", name)
+	return ph.printer.errored
 }
 
 // OnEmptyArtifact is called when an empty artifact is being uploaded.
 func (ph *TextPushHandler) OnEmptyArtifact() error {
-	return ph.printer.Println("Uploading empty artifact")
+	ph.printer.Println("Uploading empty artifact")
+	return ph.printer.errored
 }
 
 // TrackTarget returns a tracked target.