Gollum had the Ring for almost five centuries in the same cave and never got found by the Eye of Sauron.

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Sauron wasn’t at the eye until after the ring was separated from Gollum, and then was too weak to use it to scry Bilbo until the wraiths tracked him down to narrow the search… at which point it was already on its way to Mordor with a different Baggins.

primitivepal

The Eye of Sauron couldn’t get cell reception in the cave.

literally_antichrist

Also Gollum only wore it to elude orcs once he went underground. That was before Sauron started regaining his power.

Valdotain_1

imo there is a little bit of hobbit that persisted in Gollum and fought Sauron. He wasn’t totally evil, but he had been overcome with corruption like Darth Vader. Feel free to tell me I’m full of shit.

Snufflepuffster

The Eye of Sauron can’t melt steal caves!

TildaTinker