How can I retain ToolStripStatusLabel features (e.g., images, borders) when overriding OnPaint?

You'll not get the desired result by creating a custom ToolStripStatusLabel unless you draw all parts of the label yourself. The image, text, borders ...etc. Each has a set of properties that the default renderer uses to draw them in its overridable OnRenderXXX methods. Which means, you can instead create a custom renderer, override the relevant methods to draw the different parts of the label the way you want or to adjust the properties of the specialized xxxEventArgs - if possible - and call the base method to do the rest.

Take the following for example assuming the long text is set at runtime.

CSHARPCopied
public class TSRenderer : ToolStripProfessionalRenderer
{
    protected override void OnRenderItemText(ToolStripItemTextRenderEventArgs e)
    {
        if (e.Item is ToolStripStatusLabel lbl)
        {
            if (lbl.Image is not null)
            {
                Rectangle r = e.TextRectangle;
                Size scaleSize = lbl.Owner!.ImageScalingSize;

                if (r.X < scaleSize.Width)
                {
                    r.X += scaleSize.Width + 1;
                    r.Width -= r.X + 1;
                }

                e.TextRectangle = r;
            }

            e.TextFormat = TextFormatFlags.Left |
                TextFormatFlags.VerticalCenter |
                TextFormatFlags.EndEllipsis;                    
        }

        base.OnRenderItemText(e);
    }

    protected override void OnRenderItemImage(ToolStripItemImageRenderEventArgs e)
    {
        if (e.Item is ToolStripStatusLabel && e.Image is not null)
        {
            var r = e.ImageRectangle;
            r.Width = r.Height;
            r.X += 2;
            e.Graphics.DrawImage(e.Image, r);
        }
        else
        {
            base.OnRenderItemImage(e);
        }
    }
}

// Use it...

public partial class SomeForm : Form
{
    public SomeForm()
    {
        InitializeComponent();
        yourStatusStrip.Renderer = new TSRenderer();
        someToolStripStatusLabel.AutoSize = false; // Must do.
        someToolStripStatusLabel.Spring = true;
    }
}

... and that's all.

Note, when the text length exceeds the width of the available space, the base renderer does not render the image. It takes the width from the image space and appends it to the text space. Therefore, you need to override this by design behavior in the `OnRenderItemImage` method override and draw the image yourself regardless of the length of the text. This also requires overriding the `OnRenderItemText` method to - in addition to apply the required `TextFormatFlags.EndEllipsis` flag - fix the text rectangle so that it does not overlap the image rectangle since the renderer draws the image before drawing the text.

One final note, set the `ToolStripStatusLabel.AutoSize` property to `false` to ensure that overridden methods are also called when the container Form is minimized and restored. And if you need to set the long text in the designer, then make sure to set the `ToolStripStatutsLabel.AutoSize` property to `false`, the `.Text` property to the long text, and the `.Spring` property to `true` respectively.

At this point, the solution appears only at runtime. The designer does not reflect the work of the custom renderer unless you create a custom `StatusStrip`.

```csharp
public class StatusStripEx : StatusStrip
{
    protected override void OnHandleCreated(EventArgs e)
    {
        base.OnHandleCreated(e);
        Renderer = new TSRenderer();
    }
}