diff --git a/docs/Contributing/Understanding-host-vitals.md b/docs/Contributing/Understanding-host-vitals.md
index 32a4357b1e..d334aeaeeb 100644
--- a/docs/Contributing/Understanding-host-vitals.md
+++ b/docs/Contributing/Understanding-host-vitals.md
@@ -741,7 +741,11 @@ WITH app_paths AS (
 
 - Discovery query:
 ```sql
-SELECT 1 FROM osquery_info WHERE version_compare(version, '5.16.0') < 0
+SELECT 1 FROM (
+    SELECT
+    CAST(SUBSTR(version, 1, INSTR(version, '.') - 1) AS INTEGER) major,
+    CAST(SUBSTR(version, INSTR(version, '.') + 1, INSTR(SUBSTR(version, INSTR(version, '.') + 1), '.') - 1) AS INTEGER) minor from osquery_info
+) AS version_parts WHERE major < 5 OR (major = 5 AND minor < 16)
 ```
 
 - Query:
@@ -765,7 +769,11 @@ SELECT
 
 - Discovery query:
 ```sql
-SELECT 1 FROM osquery_info WHERE version_compare(version, '5.16.0') >= 0
+SELECT 1 FROM (
+    SELECT
+    CAST(substr(version, 1, instr(version, '.') - 1) AS INTEGER) major,
+    CAST(substr(version, instr(version, '.') + 1, instr(substr(version, instr(version, '.') + 1), '.') - 1) AS INTEGER) minor from osquery_info
+) AS version_parts WHERE major > 5 OR (major = 5 AND minor >= 16)
 ```
 
 - Query:
diff --git a/server/service/osquery_utils/queries.go b/server/service/osquery_utils/queries.go
index 71916c62bf..27407a68ce 100644
--- a/server/service/osquery_utils/queries.go
+++ b/server/service/osquery_utils/queries.go
@@ -1104,7 +1104,11 @@ var softwarePythonPackages = DetailQuery{
 		FROM python_packages
 	`,
 	Platforms: append(fleet.HostLinuxOSs, "darwin", "windows"),
-	Discovery: `SELECT 1 FROM osquery_info WHERE version_compare(version, '5.16.0') < 0`,
+	Discovery: `SELECT 1 FROM (
+    SELECT
+    CAST(SUBSTR(version, 1, INSTR(version, '.') - 1) AS INTEGER) major,
+    CAST(SUBSTR(version, INSTR(version, '.') + 1, INSTR(SUBSTR(version, INSTR(version, '.') + 1), '.') - 1) AS INTEGER) minor from osquery_info
+) AS version_parts WHERE major < 5 OR (major = 5 AND minor < 16)`,
 }
 
 // In osquery versions >= 5.16.0 the python_packages table was modified to allow for a
@@ -1123,7 +1127,11 @@ var softwarePythonPackagesWithUsersDir = DetailQuery{
 		FROM cached_users CROSS JOIN python_packages USING (uid)
 	`),
 	Platforms: append(fleet.HostLinuxOSs, "darwin", "windows"),
-	Discovery: `SELECT 1 FROM osquery_info WHERE version_compare(version, '5.16.0') >= 0`,
+	Discovery: `SELECT 1 FROM (
+    SELECT
+    CAST(substr(version, 1, instr(version, '.') - 1) AS INTEGER) major,
+    CAST(substr(version, instr(version, '.') + 1, instr(substr(version, instr(version, '.') + 1), '.') - 1) AS INTEGER) minor from osquery_info
+) AS version_parts WHERE major > 5 OR (major = 5 AND minor >= 16)`,
 }
 
 var softwareChrome = DetailQuery{