diff --git a/changes/17562-windows-server-2019-os-details b/changes/17562-windows-server-2019-os-details
new file mode 100644
index 000000000..e3aa773a0
--- /dev/null
+++ b/changes/17562-windows-server-2019-os-details
@@ -0,0 +1 @@
+- Fixed a bug where OS version information would not get detected on Windows Server 2019
diff --git a/server/service/osquery_utils/queries.go b/server/service/osquery_utils/queries.go
index 030294f5e..e65124e4e 100644
--- a/server/service/osquery_utils/queries.go
+++ b/server/service/osquery_utils/queries.go
@@ -172,14 +172,24 @@ var hostDetailQueries = map[string]DetailQuery{
 		},
 	},
 	"os_version_windows": {
+		// display_version is not available in some versions of
+		// Windows (Server 2019). By including it using a JOIN it can
+		// return no rows and the query will still succeed
 		Query: `
-		SELECT os.name, r.data as display_version, k.version
+		WITH display_version_table AS (
+			SELECT data as display_version
+			FROM registry
+			WHERE path = 'HKEY_LOCAL_MACHINE\\SOFTWARE\\Microsoft\\Windows NT\\CurrentVersion\\DisplayVersion'
+		)
+		SELECT
+			os.name,
+			COALESCE(d.display_version, '') AS display_version,
+			k.version
 		FROM
-			registry r,
 			os_version os,
 			kernel_info k
-		WHERE r.path = 'HKEY_LOCAL_MACHINE\\SOFTWARE\\Microsoft\\Windows NT\\CurrentVersion\\DisplayVersion'
-		`,
+		LEFT JOIN
+			display_version_table d`,
 		Platforms: []string{"windows"},
 		IngestFunc: func(ctx context.Context, logger log.Logger, host *fleet.Host, rows []map[string]string) error {
 			if len(rows) != 1 {
@@ -531,20 +541,29 @@ var extraDetailQueries = map[string]DetailQuery{
 		// This query is used to populate the `operating_systems` and `host_operating_system`
 		// tables. Separately, the `hosts` table is populated via the `os_version` and
 		// `os_version_windows` detail queries above.
+		//
+		// DisplayVersion doesn't exist on all versions of Windows (Server 2019).
+		// To prevent the query from failing in those cases, we join
+		// the values in when they exist, alternatively the column is
+		// just empty.
 		Query: `
+	WITH display_version_table AS (
+		SELECT data as display_version
+		FROM registry
+		WHERE path = 'HKEY_LOCAL_MACHINE\\SOFTWARE\\Microsoft\\Windows NT\\CurrentVersion\\DisplayVersion'
+	)
 	SELECT
 		os.name,
 		os.platform,
 		os.arch,
 		k.version as kernel_version,
 		os.version,
-		r.data as display_version
+		COALESCE(d.display_version, '') AS display_version
 	FROM
 		os_version os,
-		kernel_info k,
-		registry r
-	WHERE
-		r.path = 'HKEY_LOCAL_MACHINE\\SOFTWARE\\Microsoft\\Windows NT\\CurrentVersion\\DisplayVersion'`,
+		kernel_info k
+	LEFT JOIN
+		display_version_table d`,
 		Platforms:        []string{"windows"},
 		DirectIngestFunc: directIngestOSWindows,
 	},