diff --git a/webapp/src/app.tsx b/webapp/src/app.tsx
index 8137525ce49d..18798bb6c53b 100644
--- a/webapp/src/app.tsx
+++ b/webapp/src/app.tsx
@@ -654,6 +654,10 @@ export class ProjectView
             return;
         }
 
+        if (pxt.appTarget.simulator?.headless && !this.state.collapseEditorTools) {
+            this.toggleSimulatorCollapse();
+        }
+
         const mainBlocks = pkg.mainEditorPkg().files[pxt.MAIN_BLOCKS];
         if (this.isJavaScriptActive() || (this.shouldTryDecompile && !this.state.embedSimView))
             this.textEditor.openBlocks();
diff --git a/webapp/src/container.tsx b/webapp/src/container.tsx
index e383e047738f..30382e3809e8 100644
--- a/webapp/src/container.tsx
+++ b/webapp/src/container.tsx
@@ -114,6 +114,7 @@ export interface SettingsMenuProps extends ISettingsProps {
     greenScreen: boolean;
     accessibleBlocks: boolean;
     showShare?: boolean;
+    inBlocks: boolean;
 }
 
 // This Component overrides shouldComponentUpdate, be sure to update that if the state is updated
@@ -281,7 +282,8 @@ export class SettingsMenu extends data.Component<SettingsMenuProps, SettingsMenu
     shouldComponentUpdate(nextProps: SettingsMenuProps, nextState: SettingsMenuState, nextContext: any): boolean {
         return this.state.greenScreen != nextState.greenScreen
             || this.state.accessibleBlocks != nextState.accessibleBlocks
-            || this.state.showShare != nextState.showShare;
+            || this.state.showShare != nextState.showShare
+            || nextProps.inBlocks !== this.props.inBlocks
     }
 
     renderCore() {
@@ -296,10 +298,11 @@ export class SettingsMenu extends data.Component<SettingsMenuProps, SettingsMenu
         const disableFileAccessinMaciOs = targetTheme.disableFileAccessinMaciOs && (pxt.BrowserUtils.isIOS() || pxt.BrowserUtils.isMac())
         const disableFileAccessinAndroid = pxt.appTarget.appTheme.disableFileAccessinAndroid && pxt.BrowserUtils.isAndroid();
 
+        const headless = pxt.appTarget.simulator?.headless;
         const showHome = !targetTheme.lockedEditor && !isController && auth.hasIdentity();
         const showShare = this.props.showShare && pxt.appTarget.cloud?.sharing && !isController;
         const showSave = !readOnly && !isController && !!targetTheme.saveInMenu && !disableFileAccessinMaciOs && !disableFileAccessinAndroid;
-        const showSimCollapse = !readOnly && !isController && !!targetTheme.simCollapseInMenu;
+        const showSimCollapse = !readOnly && !isController && !!targetTheme.simCollapseInMenu && !(headless && this.props.inBlocks);
         const showGreenScreen = targetTheme.greenScreen || /greenscreen=1/i.test(window.location.href);
         const showPrint = targetTheme.print && !pxt.BrowserUtils.isIE();
         const showProjectSettings = targetTheme.showProjectSettings;
@@ -313,6 +316,8 @@ export class SettingsMenu extends data.Component<SettingsMenuProps, SettingsMenu
 
         const showCenterDivider = targetTheme.selectLanguage || targetTheme.highContrast || showGreenScreen || githubUser;
 
+        const simCollapseText = headless ? lf("Toggle the File Explorer") : lf("Toggle the simulator");
+
         return <sui.DropdownMenu role="menuitem" icon={'setting large'} title={lf("More...")} className="item icon more-dropdown-menuitem" ref={ref => this.dropdown = ref}>
             {showHome && <sui.Item className="mobile only inherit" role="menuitem" icon="home" title={lf("Home")} text={lf("Home")} ariaLabel={lf("Home screen")} onClick={this.showExitAndSaveDialog} />}
             {showShare && <sui.Item className="mobile only inherit" role="menuitem" icon="share alternate" title={lf("Publish your game to create a shareable link")} text={lf("Share")} ariaLabel={lf("Share Project")} onClick={this.showShareDialog} />}
@@ -325,7 +330,7 @@ export class SettingsMenu extends data.Component<SettingsMenuProps, SettingsMenu
             {showSave ? <sui.Item role="menuitem" icon="save" text={lf("Save Project")} onClick={this.saveProject} /> : undefined}
             {!isController ? <sui.Item role="menuitem" icon="trash" text={lf("Delete Project")} onClick={this.removeProject} /> : undefined}
             {targetTheme.timeMachine ? <sui.Item role="menuitem" icon="history" text={lf("Version History")} onClick={this.showTurnBackTimeDialog} /> : undefined}
-            {showSimCollapse ? <sui.Item role="menuitem" icon='toggle right' text={lf("Toggle the simulator")} onClick={this.toggleCollapse} /> : undefined}
+            {showSimCollapse ? <sui.Item role="menuitem" icon='toggle right' text={simCollapseText} onClick={this.toggleCollapse} /> : undefined}
             <div className="ui divider"></div>
             {targetTheme.selectLanguage ? <sui.Item icon='xicon globe' role="menuitem" text={lf("Language")} onClick={this.showLanguagePicker} /> : undefined}
             {targetTheme.highContrast ? <sui.Item role="menuitem" text={highContrast ? lf("High Contrast Off") : lf("High Contrast On")} onClick={this.toggleHighContrast} /> : undefined}
diff --git a/webapp/src/headerbar.tsx b/webapp/src/headerbar.tsx
index f2ea55ed8a71..249bf7e00ce1 100644
--- a/webapp/src/headerbar.tsx
+++ b/webapp/src/headerbar.tsx
@@ -224,7 +224,7 @@ export class HeaderBar extends data.Component<ISettingsProps, {}> {
                 return <projects.ProjectSettingsMenu parent={this.props.parent} />
             case "tutorial-tab":
             case "editor":
-                return <container.SettingsMenu parent={this.props.parent} greenScreen={greenScreen} accessibleBlocks={accessibleBlocks} showShare={!!header} />
+                return <container.SettingsMenu parent={this.props.parent} greenScreen={greenScreen} accessibleBlocks={accessibleBlocks} showShare={!!header} inBlocks={this.props.parent.isBlocksActive()} />
             default:
                 return <div />
         }