diff --git a/core/contextmenu_items.js b/core/contextmenu_items.js
index 26228ca56..560c6405e 100644
--- a/core/contextmenu_items.js
+++ b/core/contextmenu_items.js
@@ -167,7 +167,7 @@ Blockly.ContextMenuItems.registerExpand = function() {
       Blockly.ContextMenuItems.toggleOption_(false, scope.workspace.getTopBlocks(true));
     },
     scopeType: Blockly.ContextMenuRegistry.ScopeType.WORKSPACE,
-    id: 'toggleWorkspace',
+    id: 'expandWorkspace',
     weight: 0,
   };
   Blockly.ContextMenuRegistry.registry.register(expandOption);
diff --git a/tests/mocha/contextmenu_items_test.js b/tests/mocha/contextmenu_items_test.js
new file mode 100644
index 000000000..387e7083b
--- /dev/null
+++ b/tests/mocha/contextmenu_items_test.js
@@ -0,0 +1,407 @@
+/**
+ * @license
+ * Copyright 2020 Google LLC
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+suite('Context Menu Items', function() {
+  setup(function() {
+    sharedTestSetup.call(this);
+
+    // Creates a WorkspaceSVG
+    var toolbox = document.getElementById('toolbox-categories');
+    this.workspace = Blockly.inject('blocklyDiv', {toolbox: toolbox});
+
+    // Declare a new registry to ensure default options are called.
+    new Blockly.ContextMenuRegistry();
+    this.registry = Blockly.ContextMenuRegistry.registry;
+  });
+  
+  teardown(function() {
+    sharedTestTeardown.call(this);
+  });
+  
+  suite('Workspace Items', function() {
+    setup(function() {
+      this.scope = {workspace: this.workspace};
+    });
+
+    suite('undo', function() {
+      setup(function() {
+        this.undoOption = this.registry.getItem('undoWorkspace');
+      });
+
+      test('Disabled when nothing to undo', function() {
+        var precondition = this.undoOption.preconditionFn(this.scope);
+        chai.assert.equal(precondition, 'disabled',
+            'Should be disabled when there is nothing to undo');
+      });
+
+      test('Enabled when something to undo', function() {
+        // Create a new block, which should be undoable.
+        this.workspace.newBlock('text');
+        var precondition = this.undoOption.preconditionFn(this.scope);
+        chai.assert.equal(precondition, 'enabled',
+            'Should be enabled when there are actions to undo');
+      });
+
+      test('Undoes adding a new block', function() {
+        this.workspace.newBlock('text');
+        chai.assert.equal(this.workspace.getTopBlocks(false).length, 1);
+        this.undoOption.callback(this.scope);
+        chai.assert.equal(this.workspace.getTopBlocks(false).length, 0,
+            'Should be no blocks after undo');
+      });
+
+      test('Has correct label', function() {
+        chai.assert.equal(this.undoOption.displayText(), 'Undo');
+      });
+    });
+
+    suite('Redo', function() {
+      setup(function() {
+        this.redoOption = this.registry.getItem('redoWorkspace');
+      });
+
+      test('Disabled when nothing to redo', function() {
+        // Create a new block. There should be something to undo, but not redo.
+        this.workspace.newBlock('text');
+        var precondition = this.redoOption.preconditionFn(this.scope);
+        chai.assert.equal(precondition, 'disabled',
+            'Should be disabled when there is nothing to redo');
+      });
+
+      test('Enabled when something to redo', function() {
+        // Create a new block, then undo it, which means there is something to redo.
+        this.workspace.newBlock('text');
+        this.workspace.undo(false);
+        var precondition = this.redoOption.preconditionFn(this.scope);
+        chai.assert.equal(precondition, 'enabled',
+            'Should be enabled when there are actions to redo');
+      });
+
+      test('Redoes adding new block', function() {
+        // Add a new block, then undo it, then redo it.
+        this.workspace.newBlock('text');
+        this.workspace.undo(false);
+        chai.assert.equal(this.workspace.getTopBlocks(false).length, 0);
+        this.redoOption.callback(this.scope);
+        chai.assert.equal(this.workspace.getTopBlocks(false).length, 1,
+            'Should be 1 block after redo');
+      });
+
+      test('Has correct label', function() {
+        chai.assert.equal(this.redoOption.displayText(), 'Redo');
+      });
+    });
+
+    suite('Cleanup', function() {
+      setup(function() {
+        this.cleanupOption = this.registry.getItem('cleanWorkspace');
+        this.cleanupStub = sinon.stub(this.workspace, 'cleanUp');
+      });
+
+      test('Enabled when multiple blocks', function() {
+        this.workspace.newBlock('text');
+        this.workspace.newBlock('text');
+        chai.assert.equal(this.cleanupOption.preconditionFn(this.scope), 'enabled',
+            'Should be enabled if there are multiple blocks');
+      });
+
+      test('Disabled when no blocks', function() {
+        chai.assert.equal(this.cleanupOption.preconditionFn(this.scope), 'disabled',
+            'Should be disabled if there are no blocks');
+      });
+
+      test('Hidden when not movable', function() {
+        sinon.stub(this.workspace, 'isMovable').returns(false);
+        chai.assert.equal(this.cleanupOption.preconditionFn(this.scope), 'hidden',
+            'Should be hidden if the workspace is not movable');
+      });
+
+      test('Calls workspace cleanup', function() {
+        this.cleanupOption.callback(this.scope);
+        sinon.assert.calledOnce(this.cleanupStub);
+      });
+
+      test('Has correct label', function() {
+        chai.assert.equal(this.cleanupOption.displayText(), 'Clean up Blocks');
+      });
+    });
+
+    suite('Collapse', function() {
+      setup(function() {
+        this.collapseOption = this.registry.getItem('collapseWorkspace');
+      });
+
+      test('Enabled when uncollapsed blocks', function() {
+        this.workspace.newBlock('text');
+        var block2 = this.workspace.newBlock('text');
+        block2.setCollapsed(true);
+        chai.assert.equal(this.collapseOption.preconditionFn(this.scope), 'enabled',
+            'Should be enabled when any blocks are expanded');
+      });
+
+      test('Disabled when all blocks collapsed', function() {
+        this.workspace.newBlock('text').setCollapsed(true);
+        chai.assert.equal(this.collapseOption.preconditionFn(this.scope), 'disabled',
+            'Should be disabled when no blocks are expanded');
+      });
+
+      test('Hidden when no collapse option', function() {
+        var workspaceWithOptions = new Blockly.Workspace(new Blockly.Options({collapse: false}));
+        this.scope.workspace = workspaceWithOptions;
+
+        try {
+          chai.assert.equal(this.collapseOption.preconditionFn(this.scope), 'hidden',
+              'Should be hidden if collapse is disabled in options');
+        } finally {
+          workspaceTeardown.call(this, workspaceWithOptions);
+        }
+      });
+
+      test('Collapses all blocks', function() {
+        // All blocks should be collapsed, even if some already were.
+        var block1 = this.workspace.newBlock('text');
+        var block2 = this.workspace.newBlock('text');
+        // Need to render block to properly collapse it.
+        block1.initSvg();
+        block1.render();
+        block1.setCollapsed(true);
+
+        this.collapseOption.callback(this.scope);
+        this.clock.runAll();
+
+        chai.assert.isTrue(block1.isCollapsed(),
+            'Previously collapsed block should still be collapsed');
+        chai.assert.isTrue(block2.isCollapsed(),
+            'Previously expanded block should now be collapsed');
+      });
+
+      test('Has correct label', function() {
+        chai.assert.equal(this.collapseOption.displayText(), 'Collapse Blocks');
+      });
+    });
+
+    suite('Expand', function() {
+      setup(function() {
+        this.expandOption = this.registry.getItem('expandWorkspace');
+      });
+
+      test('Enabled when collapsed blocks', function() {
+        this.workspace.newBlock('text');
+        var block2 = this.workspace.newBlock('text');
+        block2.setCollapsed(true);
+
+        chai.assert.equal(this.expandOption.preconditionFn(this.scope), 'enabled',
+            'Should be enabled when any blocks are collapsed');
+      });
+
+      test('Disabled when no collapsed blocks', function() {
+        this.workspace.newBlock('text');
+        chai.assert.equal(this.expandOption.preconditionFn(this.scope), 'disabled',
+            'Should be disabled when no blocks are collapsed');
+      });
+
+      test('Hidden when no collapse option', function() {
+        var workspaceWithOptions = new Blockly.Workspace(new Blockly.Options({collapse: false}));
+        this.scope.workspace = workspaceWithOptions;
+
+        try {
+          chai.assert.equal(this.expandOption.preconditionFn(this.scope), 'hidden',
+              'Should be hidden if collapse is disabled in options');
+        } finally {
+          workspaceTeardown.call(this, workspaceWithOptions);
+        }
+      });
+
+      test('Expands all blocks', function() {
+        // All blocks should be expanded, even if some already were.
+        var block1 = this.workspace.newBlock('text');
+        var block2 = this.workspace.newBlock('text');
+        // Need to render block to properly collapse it.
+        block2.initSvg();
+        block2.render();
+        block2.setCollapsed(true);
+
+        this.expandOption.callback(this.scope);
+        this.clock.runAll();
+
+        chai.assert.isFalse(block1.isCollapsed(),
+            'Previously expanded block should still be expanded');
+        chai.assert.isFalse(block2.isCollapsed(),
+            'Previously collapsed block should now be expanded');
+      });
+
+      test('Has correct label', function() {
+        chai.assert.equal(this.expandOption.displayText(), 'Expand Blocks');
+      });
+    });
+
+    suite('Delete', function() {
+      setup(function() {
+        this.deleteOption = this.registry.getItem('workspaceDelete');
+      });
+
+      test('Enabled when blocks to delete', function() {
+        this.workspace.newBlock('text');
+        chai.assert.equal(this.deleteOption.preconditionFn(this.scope), 'enabled');
+      });
+
+      test('Disabled when no blocks to delete', function() {
+        chai.assert.equal(this.deleteOption.preconditionFn(this.scope), 'disabled');
+      });
+
+      test('Deletes all blocks after confirming', function() {
+        // Mocks the confirmation dialog and calls the callback with 'true' simulating ok.
+        var confirmStub = sinon.stub(Blockly, 'confirm').callsArgWith(1, true);
+
+        this.workspace.newBlock('text');
+        this.workspace.newBlock('text');
+        this.deleteOption.callback(this.scope);
+        this.clock.runAll();
+        sinon.assert.calledOnce(confirmStub);
+        chai.assert.equal(this.workspace.getTopBlocks(false).length, 0);
+      });
+
+      test('Does not delete blocks if not confirmed', function() {
+        // Mocks the confirmation dialog and calls the callback with 'false' simulating cancel.
+        var confirmStub = sinon.stub(Blockly, 'confirm').callsArgWith(1, false);
+
+        this.workspace.newBlock('text');
+        this.workspace.newBlock('text');
+        this.deleteOption.callback(this.scope);
+        this.clock.runAll();
+        sinon.assert.calledOnce(confirmStub);
+        chai.assert.equal(this.workspace.getTopBlocks(false).length, 2);
+      });
+
+      test('No dialog for single block', function() {
+        var confirmStub = sinon.stub(Blockly, 'confirm');
+        this.workspace.newBlock('text');
+        this.deleteOption.callback(this.scope);
+        this.clock.runAll();
+
+        sinon.assert.notCalled(confirmStub);
+        chai.assert.equal(this.workspace.getTopBlocks(false).length, 0);
+      });
+
+      test('Has correct label for multiple blocks', function() {
+        this.workspace.newBlock('text');
+        this.workspace.newBlock('text');
+
+        chai.assert.equal(this.deleteOption.displayText(this.scope), 'Delete 2 Blocks');
+      });
+
+      test('Has correct label for single block', function() {
+        this.workspace.newBlock('text');
+        chai.assert.equal(this.deleteOption.displayText(this.scope), 'Delete Block');
+      });
+    });
+  });
+
+  suite('Block Items', function() {
+    setup(function() {
+      this.block = this.workspace.newBlock('text');
+      this.scope = {block: this.block};
+    });
+
+    suite('Duplicate', function() {
+      setup(function() {
+        this.duplicateOption = this.registry.getItem('blockDuplicate');
+      });
+
+      test('Enabled when block is duplicatable', function() {
+        // Block is duplicatable by default
+        chai.assert.equal(this.duplicateOption.preconditionFn(this.scope), 'enabled');
+      });
+
+      test('Disabled when block is not dupicatable', function() {
+        sinon.stub(this.block, 'isDuplicatable').returns(false);
+        chai.assert.equal(this.duplicateOption.preconditionFn(this.scope), 'disabled');
+      });
+
+      test('Hidden when in flyout', function() {
+        this.block.isInFlyout = true;
+        chai.assert.equal(this.duplicateOption.preconditionFn(this.scope), 'hidden');
+      });
+
+      test('Calls duplicate', function() {
+        var stub = sinon.stub(Blockly, 'duplicate');
+
+        this.duplicateOption.callback(this.scope);
+
+        sinon.assert.calledOnce(stub);
+        sinon.assert.calledWith(stub, this.block);
+      });
+
+      test('Has correct label', function() {
+        chai.assert.equal(this.duplicateOption.displayText(), 'Duplicate');
+      });
+    });
+
+    suite('Comment', function() {
+      setup(function() {
+        this.commentOption = this.registry.getItem('blockComment');
+      });
+
+      test('Enabled for normal block', function() {
+        chai.assert.equal(this.commentOption.preconditionFn(this.scope), 'enabled');
+      });
+
+      test('Hidden for IE', function() {
+        var oldState = Blockly.utils.userAgent.IE;
+        try {
+          Blockly.utils.userAgent.IE = true;
+          chai.assert.equal(this.commentOption.preconditionFn(this.scope), 'hidden');
+        } finally {
+          Blockly.utils.userAgent.IE = oldState;
+        }
+      });
+
+      test('Hidden for collapsed block', function() {
+        // Must render block to collapse it properly.
+        this.block.initSvg();
+        this.block.render();
+        this.block.setCollapsed(true);
+
+        chai.assert.equal(this.commentOption.preconditionFn(this.scope), 'hidden');
+      });
+
+      test('Creates comment if one did not exist', function() {
+        chai.assert.isNull(this.block.getCommentIcon(), 'New block should not have a comment');
+        this.commentOption.callback(this.scope);
+        chai.assert.exists(this.block.getCommentIcon());
+        chai.assert.isEmpty(this.block.getCommentText(), 'Block should have empty comment text');
+      });
+
+      test('Removes comment if block had one', function() {
+        this.block.setCommentText('Test comment');
+        this.commentOption.callback(this.scope);
+        chai.assert.isNull(this.block.getCommentText(),
+            'Block should not have comment after removal');
+      });
+
+      test('Has correct label for add comment', function() {
+        chai.assert.equal(this.commentOption.displayText(this.scope), 'Add Comment');
+      });
+
+      test('Has correct label for remove comment', function() {
+        this.block.setCommentText('Test comment');
+        chai.assert.equal(this.commentOption.displayText(this.scope), 'Remove Comment');
+      });
+    });
+
+    suite('Inline Variables', function() {
+      setup(function() {
+        this.inlineOption = this.registry.getItem('blockInline');
+      });
+
+      test('Enabled when inputs to inline', function() {
+        this.block.appendValueInput('test1');
+        this.block.appendValueInput('test2');
+        chai.assert.equal(this.inlineOption.preconditionFn(this.scope), 'enabled');
+      });
+    });
+  });
+});
diff --git a/tests/mocha/index.html b/tests/mocha/index.html
index e4391e0c7..5dd168d80 100644
--- a/tests/mocha/index.html
+++ b/tests/mocha/index.html
@@ -42,6 +42,7 @@
     <script src="connection_db_test.js"></script>
     <script src="connection_checker_test.js"></script>
     <script src="connection_test.js"></script>
+    <script src="contextmenu_items_test.js"></script>
     <script src="cursor_test.js"></script>
     <script src="dropdowndiv_test.js"></script>
     <script src="event_test.js"></script>