diff --git a/src/core/server/opensearch/version_check/opensearch_opensearch_dashboards_version_compatability.test.ts b/src/core/server/opensearch/version_check/opensearch_opensearch_dashboards_version_compatability.test.ts
index 32c91d13bd5d..546ef81c23b7 100644
--- a/src/core/server/opensearch/version_check/opensearch_opensearch_dashboards_version_compatability.test.ts
+++ b/src/core/server/opensearch/version_check/opensearch_opensearch_dashboards_version_compatability.test.ts
@@ -46,6 +46,18 @@ describe('plugins/opensearch', () => {
       it('when majors are equal, but OpenSearch minor is less than OpenSearch Dashboards minor', () => {
         expect(opensearchVersionCompatibleWithOpenSearchDashboards('1.0.0', '1.1.0')).toBe(false);
       });
+
+      it('when majors and minors are not equal, but the engine is on legacy version 6.10.3 and OpenSearch Dashboards is on 1.0.0', () => {
+        expect(opensearchVersionCompatibleWithOpenSearchDashboards('6.10.3', '1.0.0')).toBe(false);
+      });
+
+      it('when majors and minors are not equal, but the engine is on legacy version 7.10.3 and OpenSearch Dashboards is on 1.0.0', () => {
+        expect(opensearchVersionCompatibleWithOpenSearchDashboards('7.10.3', '1.0.0')).toBe(false);
+      });
+
+      it('when majors and minors are not equal, but the engine is on legacy version 8.0.0 and OpenSearch Dashboards is on 1.0.0', () => {
+        expect(opensearchVersionCompatibleWithOpenSearchDashboards('8.0.0', '1.0.0')).toBe(false);
+      });
     });
 
     describe('returns true', () => {
@@ -64,6 +76,18 @@ describe('plugins/opensearch', () => {
       it('when majors and minors are equal, but OpenSearch patch is less than OpenSearch Dashboards patch', () => {
         expect(opensearchVersionCompatibleWithOpenSearchDashboards('1.1.0', '1.1.1')).toBe(true);
       });
+
+      it('when majors and minors are not equal, but the engine is on legacy version 7.10.2 and OpenSearch Dashboards is on 1.0.0', () => {
+        expect(opensearchVersionCompatibleWithOpenSearchDashboards('7.10.2', '1.0.0')).toBe(true);
+      });
+
+      it('when majors and minors are not equal, but the engine is on legacy version 7.10.2 and OpenSearch Dashboards is on 1.0.1', () => {
+        expect(opensearchVersionCompatibleWithOpenSearchDashboards('7.10.2', '1.0.1')).toBe(true);
+      });
+
+      it('when majors and minors are not equal, but the engine is on legacy version 7.10.2 and OpenSearch Dashboards is on 1.1.0', () => {
+        expect(opensearchVersionCompatibleWithOpenSearchDashboards('7.10.2', '1.1.0')).toBe(true);
+      });
     });
   });
 });
diff --git a/src/core/server/opensearch/version_check/opensearch_opensearch_dashboards_version_compatability.ts b/src/core/server/opensearch/version_check/opensearch_opensearch_dashboards_version_compatability.ts
index deaf7ba2e8d2..38f7225e35fd 100644
--- a/src/core/server/opensearch/version_check/opensearch_opensearch_dashboards_version_compatability.ts
+++ b/src/core/server/opensearch/version_check/opensearch_opensearch_dashboards_version_compatability.ts
@@ -32,6 +32,13 @@
 
 import semver, { coerce } from 'semver';
 
+/** @private */
+interface VersionNumbers {
+  major: number;
+  minor: number;
+  patch: number;
+}
+
 /**
  * Checks for the compatibilitiy between OpenSearch and OpenSearchDashboards versions
  * 1. Major version differences will never work together.
@@ -41,18 +48,27 @@ export function opensearchVersionCompatibleWithOpenSearchDashboards(
   opensearchVersion: string,
   opensearchDashboardsVersion: string
 ) {
-  const opensearchVersionNumbers = {
+  const opensearchVersionNumbers: VersionNumbers = {
     major: semver.major(opensearchVersion),
     minor: semver.minor(opensearchVersion),
     patch: semver.patch(opensearchVersion),
   };
 
-  const opensearchDashboardsVersionNumbers = {
+  const opensearchDashboardsVersionNumbers: VersionNumbers = {
     major: semver.major(opensearchDashboardsVersion),
     minor: semver.minor(opensearchDashboardsVersion),
     patch: semver.patch(opensearchDashboardsVersion),
   };
 
+  if (
+    legacyVersionCompatibleWithOpenSearchDashboards(
+      opensearchVersionNumbers,
+      opensearchDashboardsVersionNumbers
+    )
+  ) {
+    return true;
+  }
+
   // Reject mismatching major version numbers.
   if (opensearchVersionNumbers.major !== opensearchDashboardsVersionNumbers.major) {
     return false;
@@ -78,3 +94,24 @@ export function opensearchVersionEqualsOpenSearchDashboards(
     nodeSemVer.version === opensearchDashboardsSemver.version
   );
 }
+
+/**
+ * Verify legacy version of engines is compatible with current version
+ * of OpenSearch Dashboards if OpenSearch Dashboards is 1.x.
+ *
+ * @private
+ * @param legacyVersionNumbers semantic version of legacy engine
+ * @param opensearchDashboardsVersionNumbers semantic version of application
+ * @returns {boolean}
+ */
+function legacyVersionCompatibleWithOpenSearchDashboards(
+  legacyVersionNumbers: VersionNumbers,
+  opensearchDashboardsVersionNumbers: VersionNumbers
+) {
+  return (
+    legacyVersionNumbers.major === 7 &&
+    legacyVersionNumbers.minor === 10 &&
+    legacyVersionNumbers.patch === 2 &&
+    opensearchDashboardsVersionNumbers.major === 1
+  );
+}