Winbox stores all sessions on your client in one session file per router connection. Off course it's much easier always to use Check for updates instead, as this preserves the address list. If you overwrite your old Mac app without doing this, you will loose your routerlist. Import and export with Winbox ⇢ Tools ⇢ Export/Import. This means it has it's own filesystem, so if you download and install a new version, remember first to export your address list from the old app, before you might overwrite the app and all adresses with the new version. Winbox on Mac is packaged and running inside a small license-free virtual Windows installation. This works on both Windows, macOS and Linux, and is fast as it only downloads about 1.5 MB. After your first install, use Winbox ⇢ Tools ⇢ Check For Updates to upgrade to new versions.
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