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Image scaling is determined by the interaction of several properties.

size ToolStrip.ImageScalingSize

This is a the size that will be used to scale into as determined by the Items ImageScaling and the containers AutoSize setting

ToolStripItemImageScaling ToolStripItem.ImageScaling

This controls whether the image associated with this item is scaled into the size prescribed (either by the ToolStrip.ImageScalingSize or as determined by AutoSize).

 

ToolStrip AutoSize

ToolStripItem.ImageScalingMode

SizeToFit

None

TRUE

Scales to ToolStrip.ImageScalingSize

No Image Scaling
ToolStrip sizes to largest of largest item or minimum size

FALSE

Scales to area remaining in ToolStrip

No Image Scaling
No ToolStrip Sizing

Default in green.

Painting
When should I use Paint/OnPaint and when should I override the ToolStripRenderer?
Do I need to worry about double buffering?
Parenting
Partial Trust
Usage