diff --git a/circleci/docker.go b/circleci/docker.go
index 8c70676d..641665e2 100644
--- a/circleci/docker.go
+++ b/circleci/docker.go
@@ -113,7 +113,7 @@ func findNewestDockerVersion(currentVersion string, parameters *map[string]*yaml
 		cache[currentVersion] = currentTag
 		return imageName, currentTag, currentTag
 	}
-	newVersion := newest.Original()
+	newVersion := TrimSemver(currentTag, newest.Original())
 	cache[currentVersion] = newVersion
 	return imageName, currentTag, newVersion
 }
diff --git a/circleci/orb.go b/circleci/orb.go
index 0e62858e..3f0cd06c 100644
--- a/circleci/orb.go
+++ b/circleci/orb.go
@@ -67,11 +67,12 @@ func findNewestOrbVersion(currentVersion string, parameters *map[string]*yaml.No
 		return orbName, currentTag, currentTag
 	}
 
-	if len(orbInfo.Orb.HighestVersion) == 0 {
+	if len(orbInfo.Orb.HighestVersion) == 0 || strings.HasPrefix(orbInfo.Orb.HighestVersion, currentTag) {
 		cache[currentVersion] = currentTag
 		return orbName, currentTag, currentTag
 	}
 
-	cache[currentVersion] = orbInfo.Orb.HighestVersion
-	return orbName, currentTag, orbInfo.Orb.HighestVersion
+	newVersion := TrimSemver(currentTag, orbInfo.Orb.HighestVersion)
+	cache[currentVersion] = newVersion
+	return orbName, currentTag, newVersion
 }
diff --git a/circleci/update.go b/circleci/update.go
index 2e6dda47..a54af753 100644
--- a/circleci/update.go
+++ b/circleci/update.go
@@ -170,3 +170,12 @@ func ExtractParameterName(param string) string {
 	}
 	return ""
 }
+
+func TrimSemver(currentTag, newTag string) string {
+	currentSplit := strings.Split(currentTag, ".")
+	newSplit := strings.Split(newTag, ".")
+	if len(currentSplit) > len(newSplit) {
+		return newTag
+	}
+	return strings.Join(newSplit[0:len(currentSplit)], ".")
+}