diff --git a/openpype/modules/deadline/repository/custom/plugins/GlobalJobPreLoad.py b/openpype/modules/deadline/repository/custom/plugins/GlobalJobPreLoad.py
index b8a31e01ff..17f911a686 100644
--- a/openpype/modules/deadline/repository/custom/plugins/GlobalJobPreLoad.py
+++ b/openpype/modules/deadline/repository/custom/plugins/GlobalJobPreLoad.py
@@ -100,7 +100,12 @@ def inject_openpype_environment(deadlinePlugin):
         if requested_version:
             # sort detected versions
             if openpype_versions:
-                openpype_versions.sort(key=lambda ver: ver[0])
+                # use natural sorting
+                openpype_versions.sort(
+                    key=lambda ver: [
+                        int(t) if t.isdigit() else t.lower()
+                        for t in re.split('(\d+)', ver[0])
+                    ])
                 print(("*** Latest available version found is "
                        f"{openpype_versions[-1][0]}"))
             requested_major, requested_minor, _ = requested_version.split(".")[:3]  # noqa: E501
@@ -117,7 +122,11 @@ def inject_openpype_environment(deadlinePlugin):
                      "in Deadline or install it to configured "
                      "directory.").format(requested_version))
             # sort compatible versions nad pick the last one
-            compatible_versions.sort(key=lambda ver: ver[0])
+            compatible_versions.sort(
+                    key=lambda ver: [
+                        int(t) if t.isdigit() else t.lower()
+                        for t in re.split('(\d+)', ver[0])
+                    ])
             print(("*** Latest compatible version found is "
                    f"{compatible_versions[-1][0]}"))
             # create list of executables for different platform and let
diff --git a/openpype/modules/deadline/repository/custom/plugins/OpenPype/OpenPype.py b/openpype/modules/deadline/repository/custom/plugins/OpenPype/OpenPype.py
index aa3ddc7088..d270a1b87e 100644
--- a/openpype/modules/deadline/repository/custom/plugins/OpenPype/OpenPype.py
+++ b/openpype/modules/deadline/repository/custom/plugins/OpenPype/OpenPype.py
@@ -132,7 +132,11 @@ class OpenPypeDeadlinePlugin(DeadlinePlugin):
         if requested_version:
             # sort detected versions
             if openpype_versions:
-                openpype_versions.sort(key=lambda ver: ver[0])
+                openpype_versions.sort(
+                    key=lambda ver: [
+                        int(t) if t.isdigit() else t.lower()
+                        for t in re.split('(\d+)', ver[0])
+                    ])
             requested_major, requested_minor, _ = requested_version.split(".")[:3]  # noqa: E501
             compatible_versions = []
             for version in openpype_versions:
@@ -146,7 +150,11 @@ class OpenPypeDeadlinePlugin(DeadlinePlugin):
                                  "in Deadline or install it to configured "
                                  "directory.").format(requested_version))
             # sort compatible versions nad pick the last one
-            compatible_versions.sort(key=lambda ver: ver[0])
+            compatible_versions.sort(
+                    key=lambda ver: [
+                        int(t) if t.isdigit() else t.lower()
+                        for t in re.split('(\d+)', ver[0])
+                    ])
             # create list of executables for different platform and let
             # Deadline decide.
             exe_list = [