diff --git a/extensions/git/package.json b/extensions/git/package.json
index 96ece71a59f..faa5715d64c 100644
--- a/extensions/git/package.json
+++ b/extensions/git/package.json
@@ -1021,7 +1021,7 @@
         "command": "git.graph.compareWithMergeBase",
         "title": "%command.graphCompareWithMergeBase%",
         "category": "Git",
-        "enablement": "!operationInProgress && git.currentHistoryItemHasMergeBase"
+        "enablement": "!operationInProgress && scmCurrentHistoryItemRefHasBase"
       }
     ],
     "continueEditSession": [
@@ -2270,11 +2270,6 @@
           "command": "git.graph.openOutgoingChanges",
           "when": "scmProvider == git",
           "group": "1_changes@2"
-        },
-        {
-          "command": "git.graph.compareWithMergeBase",
-          "when": "scmProvider == git",
-          "group": "2_compare@1"
         }
       ],
       "scm/historyItem/context": [
@@ -2303,6 +2298,11 @@
           "when": "scmProvider == git",
           "group": "5_compare@1"
         },
+        {
+          "command": "git.graph.compareWithMergeBase",
+          "when": "scmProvider == git && scmHistoryItemHasCurrentHistoryItemRef",
+          "group": "5_compare@2"
+        },
         {
           "command": "git.copyCommitId",
           "when": "scmProvider == git && !listMultiSelection",
diff --git a/extensions/git/src/historyProvider.ts b/extensions/git/src/historyProvider.ts
index 1ed44906ab3..5c323c6acd6 100644
--- a/extensions/git/src/historyProvider.ts
+++ b/extensions/git/src/historyProvider.ts
@@ -192,7 +192,6 @@ export class GitHistoryProvider implements SourceControlHistoryProvider, FileDec
 		if (this._HEAD?.behind !== this.repository.HEAD?.behind) {
 			commands.executeCommand('setContext', 'git.currentHistoryItemIsBehind', (this.repository.HEAD?.behind ?? 0) > 0);
 		}
-		commands.executeCommand('setContext', 'git.currentHistoryItemHasMergeBase', this._currentHistoryItemBaseRef !== undefined);
 
 		this._HEAD = this.repository.HEAD;
 
diff --git a/src/vs/workbench/contrib/scm/browser/scmHistoryViewPane.ts b/src/vs/workbench/contrib/scm/browser/scmHistoryViewPane.ts
index 21a3f1e9ae0..848f02a5185 100644
--- a/src/vs/workbench/contrib/scm/browser/scmHistoryViewPane.ts
+++ b/src/vs/workbench/contrib/scm/browser/scmHistoryViewPane.ts
@@ -1531,6 +1531,7 @@ export class SCMHistoryViewPane extends ViewPane {
 
 	private readonly _scmProviderCtx: IContextKey<string | undefined>;
 	private readonly _scmCurrentHistoryItemRefHasRemote: IContextKey<boolean>;
+	private readonly _scmCurrentHistoryItemRefHasBase: IContextKey<boolean>;
 	private readonly _scmCurrentHistoryItemRefInFilter: IContextKey<boolean>;
 
 	private readonly _contextMenuDisposables = new MutableDisposable<DisposableStore>();
@@ -1559,6 +1560,7 @@ export class SCMHistoryViewPane extends ViewPane {
 
 		this._scmProviderCtx = ContextKeys.SCMProvider.bindTo(this.scopedContextKeyService);
 		this._scmCurrentHistoryItemRefHasRemote = ContextKeys.SCMCurrentHistoryItemRefHasRemote.bindTo(this.scopedContextKeyService);
+		this._scmCurrentHistoryItemRefHasBase = ContextKeys.SCMCurrentHistoryItemRefHasBase.bindTo(this.scopedContextKeyService);
 		this._scmCurrentHistoryItemRefInFilter = ContextKeys.SCMCurrentHistoryItemRefInFilter.bindTo(this.scopedContextKeyService);
 
 		this._actionRunner = this.instantiationService.createInstance(SCMHistoryViewPaneActionRunner);
@@ -1685,6 +1687,11 @@ export class SCMHistoryViewPane extends ViewPane {
 					this._scmCurrentHistoryItemRefHasRemote.set(!!historyProvider.historyItemRemoteRef.read(reader));
 				}));
 
+				// HistoryItemBaseRef changed
+				reader.store.add(autorun(reader => {
+					this._scmCurrentHistoryItemRefHasBase.set(!!historyProvider.historyItemBaseRef.read(reader));
+				}));
+
 				// ViewMode changed
 				reader.store.add(runOnChange(this._treeViewModel.viewMode, async () => {
 					await this._updateChildren();
@@ -1958,6 +1965,10 @@ export class SCMHistoryViewPane extends ViewPane {
 			// HistoryItem
 			this._contextMenuDisposables.value = new DisposableStore();
 
+			const historyProvider = element.repository.provider.historyProvider.get();
+			const historyItemRef = historyProvider?.historyItemRef.get();
+			const historyItem = element.historyItemViewModel.historyItem;
+
 			const historyItemRefMenuItems = MenuRegistry.getMenuItems(MenuId.SCMHistoryItemRefContext).filter(item => isIMenuItem(item));
 
 			// If there are any history item references we have to add a submenu item for each orignal action,
@@ -2020,9 +2031,13 @@ export class SCMHistoryViewPane extends ViewPane {
 				}
 			}
 
+			const contextKeyService = this.scopedContextKeyService.createOverlay([
+				['scmHistoryItemHasCurrentHistoryItemRef', historyItem.references?.find(ref => ref.id === historyItemRef?.id) !== undefined]
+			]);
+
 			const menuActions = this._menuService.getMenuActions(
 				MenuId.SCMHistoryItemContext,
-				this.scopedContextKeyService, {
+				contextKeyService, {
 				arg: element.repository.provider,
 				shouldForwardArgs: true
 			}).filter(group => group[0] !== 'inline');
diff --git a/src/vs/workbench/contrib/scm/browser/scmViewPane.ts b/src/vs/workbench/contrib/scm/browser/scmViewPane.ts
index 7d2cac7cb02..1b0117826d3 100644
--- a/src/vs/workbench/contrib/scm/browser/scmViewPane.ts
+++ b/src/vs/workbench/contrib/scm/browser/scmViewPane.ts
@@ -986,6 +986,7 @@ export const ContextKeys = {
 	SCMHistoryItemCount: new RawContextKey<number>('scmHistoryItemCount', 0),
 	SCMHistoryViewMode: new RawContextKey<ViewMode>('scmHistoryViewMode', ViewMode.List),
 	SCMCurrentHistoryItemRefHasRemote: new RawContextKey<boolean>('scmCurrentHistoryItemRefHasRemote', false),
+	SCMCurrentHistoryItemRefHasBase: new RawContextKey<boolean>('scmCurrentHistoryItemRefHasBase', false),
 	SCMCurrentHistoryItemRefInFilter: new RawContextKey<boolean>('scmCurrentHistoryItemRefInFilter', false),
 	RepositoryCount: new RawContextKey<number>('scmRepositoryCount', 0),
 	RepositoryVisibilityCount: new RawContextKey<number>('scmRepositoryVisibleCount', 0),