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.NET Core Version:
.NET SDK 5.0.100-rc.1.20453.7
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Have you experienced this same bug with .NET Framework?:
Yes
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More Info
The BindingNavigator/MenuStrip/ToolStrip also reproduce this issue.
Problem description:
Steps2: The focus Stay in the first Item of ToolStrip by using Tab & Shift + Tab to navigate.
Steps7: The focus both turn clockwise by using Tab & Shift + Tab to navigate now,

Expected behavior:
Steps2: The focus should turn clockwise and turn counter clockwise successfully.
Steps7: The focus should turn counter clockwise by using Shift + Tab to navigate,
Minimal repro:
- Extract "WindowsFormsApp2.zip" and open it in VS(the ToolStrip's TabStop property value is true in this project)
- Build and run the project.
- Navigate the ToolStrip by using Tab & Shift + Tab and observe.
- Stop the project and set ToolStrip's TabStop property value to false.
- Build and run the project again.
- Switch focus to TextBox item in ToolStrip.
- Using Tab & Shift + Tab to navigate ToolStrip's items and observe.
.NET Core Version:
.NET SDK 5.0.100-rc.1.20453.7
Have you experienced this same bug with .NET Framework?:
Yes
More Info
The BindingNavigator/MenuStrip/ToolStrip also reproduce this issue.
Problem description:

Steps2: The focus Stay in the first Item of ToolStrip by using Tab & Shift + Tab to navigate.
Steps7: The focus both turn clockwise by using Tab & Shift + Tab to navigate now,
Expected behavior:
Steps2: The focus should turn clockwise and turn counter clockwise successfully.
Steps7: The focus should turn counter clockwise by using Shift + Tab to navigate,
Minimal repro: