diff --git a/command/ota/upload.go b/command/ota/upload.go
index fcb32267..a41cf462 100644
--- a/command/ota/upload.go
+++ b/command/ota/upload.go
@@ -19,6 +19,7 @@ package ota
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"os"
 	"path/filepath"
@@ -101,9 +102,18 @@ func Upload(ctx context.Context, params *UploadParams, cred *config.Credentials)
 		expiration = otaDeferredExpirationMins
 	}
 
+	var conflictedOta *otaapi.Ota
 	err = iotClient.DeviceOTA(ctx, params.DeviceID, file, expiration)
 	if err != nil {
-		return err
+		if errors.Is(err, iot.ErrOtaAlreadyInProgress) {
+			conflictedOta = &otaapi.Ota{
+				DeviceID:    params.DeviceID,
+				Status:      "Skipped",
+				ErrorReason: "OTA already in progress",
+			}
+		} else {
+			return err
+		}
 	}
 	// Try to get ota-id from API
 	otaID, err := otapi.GetOtaLastStatusByDeviceID(params.DeviceID)
@@ -111,7 +121,14 @@ func Upload(ctx context.Context, params *UploadParams, cred *config.Credentials)
 		return err
 	}
 	if otaID != nil && len(otaID.Ota) > 0 {
-		feedback.PrintResult(otaID.Ota[0])
+		if conflictedOta != nil {
+			toPrint := otaapi.OtaStatusList{
+				Ota: []otaapi.Ota{*conflictedOta, otaID.Ota[0]},
+			}
+			feedback.PrintResult(toPrint)
+		} else {
+			feedback.PrintResult(otaID.Ota[0])
+		}
 	}
 
 	return nil
diff --git a/internal/iot/client.go b/internal/iot/client.go
index 55170caa..1ea50544 100644
--- a/internal/iot/client.go
+++ b/internal/iot/client.go
@@ -28,6 +28,8 @@ import (
 	"golang.org/x/oauth2"
 )
 
+var ErrOtaAlreadyInProgress = fmt.Errorf("ota already in progress")
+
 // Client can perform actions on Arduino IoT Cloud.
 type Client struct {
 	api   *iotclient.APIClient
@@ -196,9 +198,12 @@ func (cl *Client) DeviceOTA(ctx context.Context, id string, file *os.File, expir
 		Async:        optional.NewBool(true),
 	}
 	resp, err := cl.api.DevicesV2OtaApi.DevicesV2OtaUpload(ctx, id, file, opt)
-	if err != nil && resp.StatusCode != 409 { // 409 (Conflict) is the status code for an already existing OTA for the same SHA/device, so ignoring it.
-		err = fmt.Errorf("uploading device ota: %w", errorDetail(err))
-		return err
+	if err != nil {
+		// 409 (Conflict) is the status code for an already existing OTA in progress for the same device. Handling it in a different way.
+		if resp.StatusCode == 409 {
+			return ErrOtaAlreadyInProgress
+		}
+		return fmt.Errorf("uploading device ota: %w", errorDetail(err))
 	}
 	return nil
 }