If your Drawing toolbar isn't showing in TradeStation, there are two things to try to get it to appear.
Enable the Drawing Toolbar
The Drawing toolbar can be enabled or disabled, and it may be disabled by default. When a toolbar is disabled, it won't appear even when selecting a chart. You can enable the toolbar in TS 9.5 under View / Toolbars and make sure Drawing has a checkmark in front of it.
Assure a Chart is Selected
TradeStation automatically hides toolbars that don't apply to what's currently selected. TradeStation only shows the Drawing toolbar when a chart is selected. Even if you've enabled the Drawing toolbar, you must click on a chart for the Drawing toolbar to appear. This can happen quite frequently - e.g., if you use a Radar Screen in your workspace, when you select within the radar screen, the Drawing toolbar disappears, and when you click on a chart, it reappears.
In fact, this is why John and others move the Drawing toolbar from the left side of the screen and locate it above the charts, because it appears and disappears, causing the charts to compress/expand as it does.
By moving the drawing toolbar to the top of the charts, when it appears and disappears, it doesn't cause the charts to jump by a bit. You can move a toolbar by clicking the ellipses (dotted line) at the start of the toolbar. Toolbars can be placed along the borders of the chart, or they can float independently in their own window.