diff --git a/pkg/cli/predict.go b/pkg/cli/predict.go
index 911a427072..d11ae9c00b 100644
--- a/pkg/cli/predict.go
+++ b/pkg/cli/predict.go
@@ -160,6 +160,10 @@ func cmdPredict(cmd *cobra.Command, args []string) error {
 	return predictIndividualInputs(predictor, inputFlags, outPath)
 }
 
+func isURI(ref *openapi3.Schema) bool {
+	return ref != nil && ref.Type == "string" && ref.Format == "uri"
+}
+
 func predictIndividualInputs(predictor predict.Predictor, inputFlags []string, outputPath string) error {
 	console.Info("Running prediction...")
 	schema, err := predictor.GetSchema()
@@ -172,35 +176,54 @@ func predictIndividualInputs(predictor predict.Predictor, inputFlags []string, o
 		return err
 	}
 
-	prediction, err := predictor.Predict(inputs)
-	if err != nil {
-		return err
-	}
+	// Ignore @, to make it behave the same as -i
+	outputPath = strings.TrimPrefix(outputPath, "@")
 
 	// Generate output depending on type in schema
-	var out []byte
 	responseSchema := schema.Paths["/predictions"].Post.Responses["200"].Value.Content["application/json"].Schema.Value
 	outputSchema := responseSchema.Properties["output"].Value
 
-	// Multiple outputs!
-	if outputSchema.Type == "array" && outputSchema.Items.Value != nil && outputSchema.Items.Value.Type == "string" && outputSchema.Items.Value.Format == "uri" {
-		return handleMultipleFileOutput(prediction, outputSchema)
-	}
 
-	if outputSchema.Type == "string" && outputSchema.Format == "uri" {
-		dataurlObj, err := dataurl.DecodeString((*prediction.Output).(string))
+	// Multiple outputs!
+	if outputSchema.Type == "array" && isURI(outputSchema.Items.Value) {
+		prediction, err := predictor.Predict(inputs)
 		if err != nil {
-			return fmt.Errorf("Failed to decode dataurl: %w", err)
+			return err
 		}
-		out = dataurlObj.Data
-		if outputPath == "" {
-			outputPath = "output"
-			extension := mime.ExtensionByType(dataurlObj.ContentType())
-			if extension != "" {
-				outputPath += extension
+		outputs, ok := (*prediction.Output).([]interface{})
+		if !ok {
+			return fmt.Errorf("Failed to decode output")
+		}
+
+		for i, output := range outputs {
+			if err := writeDataURLOutput(output.(string), fmt.Sprintf("output.%d", i), true); err != nil {
+				return err
 			}
 		}
-	} else if outputSchema.Type == "string" {
+		return nil
+	}
+
+	// If outputPath != "", then we now know the output path for sure
+	if outputPath != "" && checkOutputWritable(outputPath) != nil {
+		return err
+	}
+
+	prediction, err := predictor.Predict(inputs)
+	if err != nil {
+		return err
+	}
+
+	if isURI(outputSchema) {
+		if outputPath == "" {
+			return writeDataURLOutput((*prediction.Output).(string), "output", true)
+		} else {
+			return writeDataURLOutput((*prediction.Output).(string), outputPath, false)
+		}
+	}
+
+	var out []byte
+
+	if outputSchema.Type == "string" {
 		// Handle strings separately because if we encode it to JSON it will be surrounded by quotes.
 		s := (*prediction.Output).(string)
 		out = []byte(s)
@@ -230,11 +253,26 @@ func predictIndividualInputs(predictor predict.Predictor, inputFlags []string, o
 	}
 
 	// Fall back to writing file
+	return writeOutput(outputPath, out)
+}
 
-	// Ignore @, to make it behave the same as -i
-	outputPath = strings.TrimPrefix(outputPath, "@")
+// Try to open the file, prevents getting errors after long prediction/training
+func checkOutputWritable(outputPath string) error {
+	outputPath, err := homedir.Expand(outputPath)
+	if err != nil {
+		return err
+	}
 
-	return writeOutput(outputPath, out)
+	// Try to open the file
+	outFile, err := os.OpenFile(outputPath, os.O_WRONLY|os.O_CREATE, 0o755)
+	if err != nil {
+		return err
+	}
+
+	if err := outFile.Close(); err != nil {
+		return err
+	}
+	return nil
 }
 
 func writeOutput(outputPath string, output []byte) error {
@@ -244,7 +282,7 @@ func writeOutput(outputPath string, output []byte) error {
 	}
 
 	// Write to file
-	outFile, err := os.OpenFile(outputPath, os.O_WRONLY|os.O_CREATE, 0o755)
+	outFile, err := os.OpenFile(outputPath, os.O_WRONLY|os.O_CREATE|os.O_TRUNC, 0o755)
 	if err != nil {
 		return err
 	}
@@ -259,26 +297,21 @@ func writeOutput(outputPath string, output []byte) error {
 	return nil
 }
 
-func handleMultipleFileOutput(prediction *predict.Response, outputSchema *openapi3.Schema) error {
-	outputs, ok := (*prediction.Output).([]interface{})
-	if !ok {
-		return fmt.Errorf("Failed to decode output")
+func writeDataURLOutput(outputString string, outputPath string, addExtension bool) error {
+	dataurlObj, err := dataurl.DecodeString(outputString)
+	if err != nil {
+		return fmt.Errorf("Failed to decode dataurl: %w", err)
 	}
-
-	for i, output := range outputs {
-		outputString := output.(string)
-		dataurlObj, err := dataurl.DecodeString(outputString)
-		if err != nil {
-			return fmt.Errorf("Failed to decode dataurl: %w", err)
-		}
-		out := dataurlObj.Data
+	out := dataurlObj.Data
+	if addExtension {
 		extension := mime.ExtensionByType(dataurlObj.ContentType())
-		outputPath := fmt.Sprintf("output.%d%s", i, extension)
-		if err := writeOutput(outputPath, out); err != nil {
-			return err
+		if extension != "" {
+			outputPath += extension
 		}
 	}
-
+	if err := writeOutput(outputPath, out); err != nil {
+		return err
+	}
 	return nil
 }