diff --git a/pkg/cluster/cluster.go b/pkg/cluster/cluster.go
index 1ee54d75..54e91abc 100644
--- a/pkg/cluster/cluster.go
+++ b/pkg/cluster/cluster.go
@@ -1245,13 +1245,18 @@ func (c *Cluster) Update(oldSpec, newSpec *cpov1.Postgresql) error {
 	}
 
 	if !updateFailed {
-		// Major version upgrade must only fire after success of earlier operations and should stay last
-		if err := c.majorVersionUpgrade(); err != nil {
-			c.logger.Errorf("major version upgrade failed: %v", err)
+		if upgradeErr := c.executeMajorVersionUpgrade(); upgradeErr != nil {
+			c.logger.Errorf("major version upgrade failed: %v", upgradeErr)
 			updateFailed = true
 		}
 	}
 
+	if updateFailed {
+		c.logger.Errorf("Update for cluster %s/%s finished with errors..", c.Namespace, c.Name)
+	} else {
+		c.logger.Infof("Update for cluster %s/%s completed successfully.", c.Namespace, c.Name)
+	}
+
 	return nil
 }
 
diff --git a/pkg/cluster/majorversionupgrade.go b/pkg/cluster/majorversionupgrade.go
index 61edf190..5f204af0 100644
--- a/pkg/cluster/majorversionupgrade.go
+++ b/pkg/cluster/majorversionupgrade.go
@@ -3,8 +3,10 @@ package cluster
 import (
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"strings"
+	"time"
 
 	"github.com/Masterminds/semver"
 	"github.com/cybertec-postgresql/cybertec-pg-operator/pkg/spec"
@@ -29,6 +31,8 @@ const (
 	majorVersionUpgradeFailureAnnotation = "last-major-upgrade-failure"
 )
 
+var errUpgradePrepNotReady = errors.New("cluster not ready for upgrade")
+
 // IsBiggerPostgresVersion Compare two Postgres version numbers
 func IsBiggerPostgresVersion(old string, new string) bool {
 	oldN := VersionMap[old]
@@ -232,12 +236,14 @@ func (c *Cluster) majorVersionUpgrade() error {
 			continue
 		}
 		if checkStreaming && member.State != "streaming" {
-			c.logger.Infof("skipping major version upgrade, replica %s is not streaming from primary", member.Name)
-			return nil
+			// c.logger.Infof("skipping major version upgrade, replica %s is not streaming from primary", member.Name)
+			// return nil
+			return fmt.Errorf("%w: replica %s is not streaming (state: %s)", errUpgradePrepNotReady, member.Name, member.State)
 		}
 		if member.Lag > 16*1024*1024 {
-			c.logger.Infof("skipping major version upgrade, replication lag on member %s is too high", member.Name)
-			return nil
+			// c.logger.Infof("skipping major version upgrade, replication lag on member %s is too high", member.Name)
+			// return nil
+			return fmt.Errorf("%w: replication lag on member %s is too high (%d bytes)", errUpgradePrepNotReady, member.Name, member.Lag)
 		}
 	}
 
@@ -246,11 +252,10 @@ func (c *Cluster) majorVersionUpgrade() error {
 	if allRunning {
 		c.logger.Infof("healthy cluster ready to upgrade, current: %d desired: %d", c.currentMajorVersion, desiredVersion)
 		if c.currentMajorVersion < desiredVersion {
-			defer func() error {
-				if err = c.criticalOperationLabel(pods, nil); err != nil {
-					return fmt.Errorf("failed to remove critical-operation label: %s", err)
+			defer func() {
+				if err := c.criticalOperationLabel(pods, nil); err != nil {
+					c.logger.Errorf("failed to remove critical-operation label: %v", err)
 				}
-				return nil
 			}()
 			val := "true"
 			if err = c.criticalOperationLabel(pods, &val); err != nil {
@@ -260,37 +265,72 @@ func (c *Cluster) majorVersionUpgrade() error {
 			podName := &spec.NamespacedName{Namespace: masterPod.Namespace, Name: masterPod.Name}
 			c.logger.Infof("triggering major version upgrade on pod %s of %d pods", masterPod.Name, numberOfPods)
 			c.eventRecorder.Eventf(c.GetReference(), v1.EventTypeNormal, "Major Version Upgrade", "starting major version upgrade on pod %s of %d pods", masterPod.Name, numberOfPods)
-			upgradeCommand := fmt.Sprintf("set -o pipefail && /usr/bin/python3 /scripts/inplace_upgrade.py %d 2>&1 | tee last_upgrade.log", numberOfPods)
-
-			c.logger.Debug("checking if the spilo image runs with root or non-root (check for user id=0)")
+			upgradeCommand := fmt.Sprintf("/usr/local/bin/python3 /scripts/inplace_upgrade.py %d 2>&1", numberOfPods)
+			c.logger.Debug("checking if the container runs with root or non-root (check for user id=0)")
 			resultIdCheck, errIdCheck := c.ExecCommand(podName, "/bin/bash", "-c", "/usr/bin/id -u")
 			if errIdCheck != nil {
 				c.eventRecorder.Eventf(c.GetReference(), v1.EventTypeWarning, "Major Version Upgrade", "checking user id to run upgrade from %d to %d FAILED: %v", c.currentMajorVersion, desiredVersion, errIdCheck)
 			}
 
 			resultIdCheck = strings.TrimSuffix(resultIdCheck, "\n")
-			var result, scriptErrMsg string
+			var result string
+
 			if resultIdCheck != "0" {
 				c.logger.Infof("user id was identified as: %s, hence default user is non-root already", resultIdCheck)
 				result, err = c.ExecCommand(podName, "/bin/bash", "-c", upgradeCommand)
-				scriptErrMsg, _ = c.ExecCommand(podName, "/bin/bash", "-c", "tail -n 1 last_upgrade.log")
 			} else {
 				c.logger.Infof("user id was identified as: %s, using su to reach the postgres user", resultIdCheck)
 				result, err = c.ExecCommand(podName, "/bin/su", "postgres", "-c", upgradeCommand)
-				scriptErrMsg, _ = c.ExecCommand(podName, "/bin/bash", "-c", "tail -n 1 last_upgrade.log")
 			}
+
 			if err != nil {
 				isUpgradeSuccess = false
 				c.annotatePostgresResource(isUpgradeSuccess)
-				c.eventRecorder.Eventf(c.GetReference(), v1.EventTypeWarning, "Major Version Upgrade", "upgrade from %d to %d FAILED: %v", c.currentMajorVersion, desiredVersion, scriptErrMsg)
-				return fmt.Errorf("%s", scriptErrMsg)
+
+				finalErrorMsg := strings.TrimSpace(result)
+				if finalErrorMsg == "" {
+					finalErrorMsg = err.Error()
+				}
+
+				lines := strings.Split(finalErrorMsg, "\n")
+				if len(lines) > 5 {
+					finalErrorMsg = strings.Join(lines[len(lines)-5:], " | ")
+				}
+
+				c.logger.Errorf("Major upgrade failed: %v", err)
+				c.eventRecorder.Eventf(c.GetReference(), v1.EventTypeWarning, "Major Version Upgrade", "upgrade from %d to %d FAILED: %s", c.currentMajorVersion, desiredVersion, finalErrorMsg)
+
+				return fmt.Errorf("upgrade script failed: %s", finalErrorMsg)
 			}
 
 			c.annotatePostgresResource(isUpgradeSuccess)
 			c.logger.Infof("upgrade action triggered and command completed: %s", result[:100])
-			c.eventRecorder.Eventf(c.GetReference(), v1.EventTypeNormal, "Major Version Upgrade", "upgrade from %d to %d finished", c.currentMajorVersion, desiredVersion)
+			c.eventRecorder.Eventf(c.GetReference(), v1.EventTypeNormal, "Major Version Upgrade", "major version upgrade from version %d to version %d was successfully completed.", c.currentMajorVersion, desiredVersion)
 		}
 	}
 
 	return nil
 }
+
+func (c *Cluster) executeMajorVersionUpgrade() error {
+	maxRetries := 6
+	var lastErr error
+
+	for i := 0; i < maxRetries; i++ {
+		lastErr = c.majorVersionUpgrade()
+		if lastErr == nil {
+			return nil
+		}
+
+		if errors.Is(lastErr, errUpgradePrepNotReady) {
+			c.logger.Warnf("Major version upgrade deferred (attempt %d/%d): %v. Retrying in 15s...", i+1, maxRetries, lastErr)
+
+			if i < maxRetries-1 {
+				time.Sleep(15 * time.Second)
+				continue
+			}
+		}
+		return lastErr
+	}
+	return lastErr
+}
diff --git a/pkg/cluster/sync.go b/pkg/cluster/sync.go
index 7ebcc8b8..11e18adb 100644
--- a/pkg/cluster/sync.go
+++ b/pkg/cluster/sync.go
@@ -172,6 +172,7 @@ func generateSerialNumber() (*big.Int, error) {
 // Unlike the update, sync does not error out if some objects do not exist and takes care of creating them.
 func (c *Cluster) Sync(newSpec *cpov1.Postgresql) error {
 	var err error
+	syncFailed := false
 	c.mu.Lock()
 	defer c.mu.Unlock()
 
@@ -326,9 +327,21 @@ func (c *Cluster) Sync(newSpec *cpov1.Postgresql) error {
 		}
 	}
 
-	// Major version upgrade must only run after success of all earlier operations, must remain last item in sync
-	if err := c.majorVersionUpgrade(); err != nil {
-		c.logger.Errorf("major version upgrade failed: %v", err)
+	if err != nil {
+		syncFailed = true
+	}
+	if !syncFailed {
+		err = c.executeMajorVersionUpgrade()
+		if err != nil {
+			c.logger.Errorf("major version upgrade failed after retries: %v", err)
+			syncFailed = true
+		}
+	}
+
+	if syncFailed {
+		c.logger.Errorf("Update for cluster %s/%s finished with errors..", c.Namespace, c.Name)
+	} else {
+		c.logger.Infof("Update for cluster %s/%s completed successfully.", c.Namespace, c.Name)
 	}
 
 	return err
diff --git a/ui/Dockerfile b/ui/Dockerfile
index 63e8817e..37abc7c8 100644
--- a/ui/Dockerfile
+++ b/ui/Dockerfile
@@ -38,4 +38,4 @@ ARG VERSION=dev
 RUN sed -i "s/__version__ = .*/__version__ = '${VERSION}'/" /operator_ui/__init__.py
 
 WORKDIR /
-CMD ["/usr/bin/python3", "-m", "operator_ui"]
+CMD ["/usr/local/bin/python3", "-m", "operator_ui"]
diff --git a/ui/start_server.sh b/ui/start_server.sh
index e2c3980c..7ed2546c 100644
--- a/ui/start_server.sh
+++ b/ui/start_server.sh
@@ -1,2 +1,2 @@
 #!/bin/bash
-/usr/bin/python3 -m operator_ui
+/usr/local/bin/python3 -m operator_ui