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The HOA charged every unit $8,500 to fix the building's roof. Her condo insurance covered $1,000 of it. She owed the other $7,500 herself.

The HOA charged every unit $8,500 to fix the building’s roof....

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Her SUV was gone from the apartment lot by morning. Insurance replaced the car, but not the $4,500 of belongings that vanished with it.

Her SUV was gone from the apartment lot by morning. Insurance...

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His insurer offered to settle the lawsuit for $120,000. He wanted to clear his name. The clause he never read meant fighting could cost him $210,000 out of pocket.

His insurer offered to settle the lawsuit for $120,000. He wanted...

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She hit Medicare's new $2,100 drug cap in June. Her August pharmacy bill was still $900.

She hit Medicare’s new $2,100 drug cap in June. Her August...

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A storm flooded her ground-floor apartment and ruined $9,000 of belongings. Her renters policy paid nothing.

A storm flooded her ground-floor apartment and ruined $9,000 of belongings....

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A fire closed her cafe for four months. Her insurance stopped paying the day the repairs finished, while sales were still down by half.

A fire closed her cafe for four months. Her insurance stopped...

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He was told the policy would 'pay for itself' by 70. At 68 the insurer asked for $9,000 or it would lapse.

He was told the policy would ‘pay for itself’ by 70....

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A kitchen fire destroyed everything the Reyes family owned. Their insurer paid $41,000 on a $90,000 loss.

A kitchen fire destroyed everything the Reyes family owned. Their insurer...

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He leased on 12 owner-operators to cut his workers' comp bill. One rollover left him owing $380,000.

He leased on 12 owner-operators to cut his workers’ comp bill....

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A new windshield cost her $320. The recalibration she skipped nearly cost far more

A new windshield cost her $320. The recalibration she skipped nearly...

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