The latest incident took place around 6:30 a.m. Tuesday in Greenwich at the Steamboat Road railroad overpass, said Greenwich Police.
The truck's roof was torn off but managed to make it out from under the bridge.
The same overpass was hit on June 29 when another truck almost tore its roof off passing under the bridge.
Greenwich police said the bridge has been struck repeatedly over the years due to the driver's not reading the height signs.
Local officials have been working to eradicate the problem by attempting to make sure that GPS systems and mapping software used by truckers is updated to alert them to lower passings.
The overpass is owned by the MTA, which handled crashes.
The latest truck to strike the overpass belonged to Creative Installations.
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