diff --git a/cli/cmd/deploy.go b/cli/cmd/deploy.go
index ce4c23c877..53882fa216 100644
--- a/cli/cmd/deploy.go
+++ b/cli/cmd/deploy.go
@@ -120,16 +120,22 @@ var _deployCmd = &cobra.Command{
 				exit.Error(err)
 			}
 			fmt.Println(string(bytes))
-			return
 		case flags.MixedOutputType:
 			err := mixedPrint(deployResults)
 			if err != nil {
 				exit.Error(err)
 			}
-			return
 		case flags.PrettyOutputType:
 			message := deployMessage(deployResults, env.Name)
-			print.BoldFirstBlock(message)
+			if didAnyResultsError(deployResults) {
+				print.StderrBoldFirstBlock(message)
+			} else {
+				print.BoldFirstBlock(message)
+			}
+		}
+
+		if didAnyResultsError(deployResults) {
+			exit.Error(nil)
 		}
 	},
 }
@@ -297,6 +303,15 @@ func didAllResultsError(results []schema.DeployResult) bool {
 	return true
 }
 
+func didAnyResultsError(results []schema.DeployResult) bool {
+	for _, result := range results {
+		if result.Error != "" {
+			return true
+		}
+	}
+	return false
+}
+
 func getAPICommandsMessage(results []schema.DeployResult, envName string) string {
 	apiName := "<api_name>"
 	if len(results) == 1 {
diff --git a/pkg/lib/errors/message.go b/pkg/lib/errors/message.go
index 6606f183cb..c174adf5b2 100644
--- a/pkg/lib/errors/message.go
+++ b/pkg/lib/errors/message.go
@@ -17,7 +17,6 @@ limitations under the License.
 package errors
 
 import (
-	"os"
 	"strings"
 
 	"github.com/aws/aws-sdk-go/aws/awserr"
@@ -25,7 +24,7 @@ import (
 )
 
 func PrintError(err error, strs ...string) {
-	os.Stderr.WriteString(ErrorStr(err, strs...) + "\n")
+	print.StderrPrintln(ErrorStr(err, strs...))
 	// PrintStacktrace(err)
 }
 
diff --git a/pkg/lib/exit/exit.go b/pkg/lib/exit/exit.go
index 78564a04bb..86af746d16 100644
--- a/pkg/lib/exit/exit.go
+++ b/pkg/lib/exit/exit.go
@@ -33,11 +33,11 @@ func Error(err error, wrapStrs ...string) {
 		err = errors.Wrap(err, str)
 	}
 
-	if !errors.IsNoTelemetry(err) {
+	if err != nil && !errors.IsNoTelemetry(err) {
 		telemetry.Error(err)
 	}
 
-	if !errors.IsNoPrint(err) {
+	if err != nil && !errors.IsNoPrint(err) {
 		errors.PrintErrorForUser(err)
 	}
 
@@ -51,7 +51,7 @@ func Panic(err error, wrapStrs ...string) {
 		err = errors.Wrap(err, str)
 	}
 
-	if !errors.IsNoTelemetry(err) {
+	if err != nil && !errors.IsNoTelemetry(err) {
 		telemetry.Error(err)
 	}
 
diff --git a/pkg/lib/print/print.go b/pkg/lib/print/print.go
index b5942064da..7445043949 100644
--- a/pkg/lib/print/print.go
+++ b/pkg/lib/print/print.go
@@ -45,14 +45,14 @@ func StderrBoldFirstLine(msg string) {
 	msgParts := strings.Split(msg, "\n")
 
 	if len(msgParts[0]) > _maxBoldLength {
-		os.Stderr.WriteString(msg + "\n")
+		StderrPrintln(msg)
 		return
 	}
 
-	os.Stderr.WriteString(console.Bold(msgParts[0]) + "\n")
+	StderrPrintln(console.Bold(msgParts[0]))
 
 	if len(msgParts) > 1 {
-		os.Stderr.WriteString(strings.Join(msgParts[1:], "\n") + "\n")
+		StderrPrintln(strings.Join(msgParts[1:], "\n"))
 	}
 }
 
@@ -71,7 +71,26 @@ func BoldFirstBlock(msg string) {
 	}
 }
 
+func StderrBoldFirstBlock(msg string) {
+	msgParts := strings.Split(msg, "\n\n")
+
+	if len(msgParts[0]) > _maxBoldLength {
+		StderrPrintln(msg)
+		return
+	}
+
+	StderrPrintln(console.Bold(msgParts[0]))
+
+	if len(msgParts) > 1 {
+		StderrPrintln("\n" + strings.Join(msgParts[1:], "\n\n"))
+	}
+}
+
 func Dot() error {
 	fmt.Print(".")
 	return nil
 }
+
+func StderrPrintln(str string) {
+	os.Stderr.WriteString(str + "\n")
+}
diff --git a/pkg/workloads/cortex/client/cortex/binary/__init__.py b/pkg/workloads/cortex/client/cortex/binary/__init__.py
index f7cf580015..2cd4fc2c5a 100644
--- a/pkg/workloads/cortex/client/cortex/binary/__init__.py
+++ b/pkg/workloads/cortex/client/cortex/binary/__init__.py
@@ -77,6 +77,7 @@ def run_cli(
                 result = "~"
                 output = output[:-1]
             if result_found:
+                output = output[:-1]
                 if c == "\n":
                     result_found = False
                     result = result[len(MIXED_CORTEX_MARKER) : -len(MIXED_CORTEX_MARKER)]
@@ -96,6 +97,9 @@ def run_cli(
             return result
         return output
 
+    if result != "":
+        raise CortexBinaryException(result + "\n" + process.stderr.read())
+
     raise CortexBinaryException(process.stderr.read())