diff --git a/worker/alerts.go b/worker/alerts.go
index fd3657e05..5ab5092b7 100644
--- a/worker/alerts.go
+++ b/worker/alerts.go
@@ -1,6 +1,7 @@
 package worker
 
 import (
+	"errors"
 	"time"
 
 	"go.sia.tech/core/types"
@@ -49,6 +50,18 @@ func newUploadFailedAlert(bucket, path, contractSet, mimeType string, minShards,
 		data["multipart"] = true
 	}
 
+	hostErr := err
+	for errors.Unwrap(hostErr) != nil {
+		hostErr = errors.Unwrap(hostErr)
+	}
+	if set, ok := hostErr.(HostErrorSet); ok {
+		hostErrors := make(map[string]string, len(set))
+		for hk, err := range set {
+			hostErrors[hk.String()] = err.Error()
+		}
+		data["hosts"] = hostErrors
+	}
+
 	return alerts.Alert{
 		ID:        randomAlertID(),
 		Severity:  alerts.SeverityError,
diff --git a/worker/alerts_test.go b/worker/alerts_test.go
new file mode 100644
index 000000000..137838a39
--- /dev/null
+++ b/worker/alerts_test.go
@@ -0,0 +1,48 @@
+package worker
+
+import (
+	"errors"
+	"fmt"
+	"testing"
+	"time"
+
+	"github.com/google/go-cmp/cmp"
+	"go.sia.tech/core/types"
+	"go.sia.tech/renterd/alerts"
+)
+
+// TestUploadFailedAlertErrorSet is a test to verify that an upload failing with a HostErrorSet error registers an alert with all the individual errors of any host in the payload.
+func TestUploadFailedAlertErrorSet(t *testing.T) {
+	hostErrSet := HostErrorSet{
+		types.PublicKey{1, 1, 1}: errors.New("test"),
+	}
+	wrapped := fmt.Errorf("wrapped error: %w", hostErrSet)
+
+	alert := newUploadFailedAlert("bucket", "path", "set", "mimeType", 1, 2, 3, true, false, wrapped)
+
+	alert.ID = types.Hash256{1, 2, 3}
+	alert.Timestamp = time.Time{}
+
+	expectedAlert := alerts.Alert{
+		ID:       types.Hash256{1, 2, 3},
+		Severity: alerts.SeverityError,
+		Message:  "Upload failed",
+		Data: map[string]any{
+			"bucket":      "bucket",
+			"contractSet": "set",
+			"contracts":   3,
+			"error":       wrapped.Error(),
+			"hosts": map[string]string{
+				types.PublicKey{1, 1, 1}.String(): "test",
+			},
+			"mimeType":    "mimeType",
+			"minShards":   1,
+			"packing":     true,
+			"path":        "path",
+			"totalShards": 2,
+		},
+	}
+	if !cmp.Equal(alert, expectedAlert) {
+		t.Fatal(cmp.Diff(alert, expectedAlert))
+	}
+}