diff --git a/artifactory/services/system.go b/artifactory/services/system.go
index 2337590c2..3144637f3 100644
--- a/artifactory/services/system.go
+++ b/artifactory/services/system.go
@@ -122,7 +122,7 @@ func (ss *SystemService) sendGet(endpoint string) ([]byte, error) {
 		return nil, err
 	}
 	if err = errorutils.CheckResponseStatusWithBody(resp, body, http.StatusOK, http.StatusCreated); err != nil {
-		return nil, fmt.Errorf("failed while attempting to get Artifactory %s:\n%s", endpoint, err.Error())
+		return nil, fmt.Errorf("got unexpected server response while attempting to get JFrog Artifactory %s:\n%s", endpoint, err.Error())
 	}
 	log.Debug("Artifactory response:", resp.Status)
 	return body, nil
diff --git a/distribution/services/version.go b/distribution/services/version.go
index c3cd4ac72..18e205c04 100644
--- a/distribution/services/version.go
+++ b/distribution/services/version.go
@@ -28,11 +28,11 @@ func (vs *VersionService) GetDistributionVersion() (string, error) {
 	httpDetails := vs.DistDetails.CreateHttpClientDetails()
 	resp, body, _, err := vs.client.SendGet(vs.DistDetails.GetUrl()+"api/v1/system/info", true, &httpDetails)
 	if err != nil {
-		return "", errors.New("failed while attempting to get Distribution version: " + err.Error())
+		return "", errors.New("failed while attempting to get JFrog Distribution version: " + err.Error())
 	}
 
 	if err = errorutils.CheckResponseStatusWithBody(resp, body, http.StatusOK); err != nil {
-		return "", errors.New("failed while attempting to get JFrog Distribution version:\n" + err.Error())
+		return "", errors.New("got unexpected server response while attempting to get JFrog Distribution version:\n" + err.Error())
 	}
 	var version distributionVersion
 	if err = json.Unmarshal(body, &version); err != nil {
diff --git a/pipelines/services/system.go b/pipelines/services/system.go
index 47578ca36..17ad24439 100644
--- a/pipelines/services/system.go
+++ b/pipelines/services/system.go
@@ -25,13 +25,13 @@ func (ss *SystemService) GetSystemInfo() (*PipelinesSystemInfo, error) {
 	httpDetails := ss.ServiceDetails.CreateHttpClientDetails()
 	resp, body, _, err := ss.client.SendGet(ss.ServiceDetails.GetUrl()+"api/v1/system/info", true, &httpDetails)
 	if err != nil {
-		return nil, errors.New("failed while attempting to get Pipelines version: " + err.Error())
+		return nil, errors.New("failed while attempting to get JFrog Pipelines version: " + err.Error())
 	}
 	if err = errorutils.CheckResponseStatusWithBody(resp, body, http.StatusOK); err != nil {
 		if resp.StatusCode == http.StatusNotFound {
 			return nil, &PipelinesNotAvailableError{InnerError: err}
 		}
-		return nil, errors.New("failed while attempting to get JFrog Pipelines version:\n" + err.Error())
+		return nil, errors.New("got unexpected server response while attempting to get JFrog Pipelines version:\n" + err.Error())
 	}
 	var sysInfo PipelinesSystemInfo
 	if err = json.Unmarshal(body, &sysInfo); err != nil {
diff --git a/xray/services/entitlements.go b/xray/services/entitlements.go
index e0ddb9835..255397208 100644
--- a/xray/services/entitlements.go
+++ b/xray/services/entitlements.go
@@ -2,6 +2,7 @@ package services
 
 import (
 	"encoding/json"
+	"errors"
 	"fmt"
 	"net/http"
 
@@ -30,10 +31,11 @@ func (es *EntitlementsService) IsEntitled(featureId string) (entitled bool, err
 	httpDetails := es.XrayDetails.CreateHttpClientDetails()
 	resp, body, _, err := es.client.SendGet(es.XrayDetails.GetUrl()+"api/v1/entitlements/feature/"+featureId, true, &httpDetails)
 	if err != nil {
+		err = errors.New("failed while attempting to get JFrog Xray entitlements response: " + err.Error())
 		return
 	}
 	if err = errorutils.CheckResponseStatusWithBody(resp, body, http.StatusOK); err != nil {
-		return false, fmt.Errorf("failed while attempting to get JFrog Xray entitlements response for %s:\n%s", featureId, err.Error())
+		return false, fmt.Errorf("got unexpected server response while attempting to get JFrog Xray entitlements response for %s:\n%s", featureId, err.Error())
 	}
 	var userEntitlements entitlements
 	if err = json.Unmarshal(body, &userEntitlements); err != nil {
diff --git a/xray/services/version.go b/xray/services/version.go
index f5a771ba7..a9bee460f 100644
--- a/xray/services/version.go
+++ b/xray/services/version.go
@@ -32,10 +32,10 @@ func (vs *VersionService) GetVersion() (string, error) {
 	httpDetails := vs.XrayDetails.CreateHttpClientDetails()
 	resp, body, _, err := vs.client.SendGet(vs.XrayDetails.GetUrl()+"api/v1/system/version", true, &httpDetails)
 	if err != nil {
-		return "", errors.New("failed while attempting to get Xray version: " + err.Error())
+		return "", errors.New("failed while attempting to get JFrog Xray version: " + err.Error())
 	}
 	if err = errorutils.CheckResponseStatusWithBody(resp, body, http.StatusOK); err != nil {
-		return "", errors.New("failed while attempting to get JFrog Xray version:\n" + err.Error())
+		return "", errors.New("got unexpected server response while attempting to get JFrog Xray version:\n" + err.Error())
 	}
 	var version xrayVersion
 	if err = json.Unmarshal(body, &version); err != nil {