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Preparing Your Home for Winter: When to Hire Contractors

As temperatures drop and winter approaches, preparing your home for the harsh conditions ahead isn’t just about comfort—it’s about protecting your most valuable investment. While some winterization tasks are perfect DIY projects, others require professional contractors to ensure safety, efficiency, and long-term protection.

This comprehensive guide helps you understand which winter preparation projects you can handle yourself and when it’s essential to hire a professional contractor.

Table of Contents

Why Winter Preparation Matters

Failing to properly winterize your home can lead to:

  • Frozen and burst pipes: Causing thousands in water damage
  • Ice dams: Damaging roofs, gutters, and interiors
  • Higher energy bills: From heat loss and inefficient systems
  • HVAC breakdowns: When you need heat most
  • Structural damage: From moisture infiltration and freezing
  • Safety hazards: Carbon monoxide risks, fire dangers
  • Pest infestations: Seeking warmth in your home

The cost of prevention is always less than the cost of repair.

DIY Winter Preparation Tasks

These projects are safe and effective for homeowners to tackle themselves:

1. Weather Stripping and Caulking

Difficulty: Easy
Time: 2-4 hours
Cost: $50-$150
Savings vs. Professional: 80-90%

What you need:

  • Weatherstripping (foam, V-strip, or rubber)
  • Exterior caulk (for outside)
  • Interior caulk (for inside)
  • Caulk gun
  • Utility knife

How to do it:

  • Inspect all windows and doors for gaps
  • Remove old, damaged weatherstripping
  • Apply new weatherstripping to door frames
  • Caulk around window frames (inside and out)
  • Seal gaps around pipes, vents, and electrical outlets
  • Check basement rim joists for air leaks

Pro tip: Do this on a mild day (50-70°F) for proper caulk adhesion.

2. Cleaning Gutters and Downspouts

Difficulty: Easy to Moderate
Time: 2-5 hours
Cost: $0-$50 (if you have a ladder)
Savings vs. Professional: 70-85%

Why it’s important: Clogged gutters cause ice dams, foundation damage, and roof leaks.

How to do it:

  • Use a sturdy ladder with someone spotting you
  • Remove leaves, twigs, and debris by hand or with a scoop
  • Flush gutters and downspouts with a garden hose
  • Ensure downspouts direct water at least 5 feet from foundation
  • Check for loose or damaged gutters
  • Consider installing gutter guards

When to hire a pro:

  • Multi-story homes (safety concern)
  • Steep roof pitches
  • You’re uncomfortable on ladders
  • Gutters need repairs or replacement

3. Reversing Ceiling Fan Direction

Difficulty: Very Easy
Time: 5 minutes per fan
Cost: $0
Savings: Lower heating bills

How it works: Ceiling fans have a switch that reverses blade direction. In winter, fans should run clockwise (looking up) at low speed to push warm air down from the ceiling.

Instructions:

  • Turn off fan and wait for blades to stop
  • Locate the direction switch on the motor housing
  • Flip switch to reverse direction
  • Run fan at low speed

Energy savings: Can reduce heating costs by 10-15%.

4. Insulating Pipes

Difficulty: Easy
Time: 1-3 hours
Cost: $20-$100
Savings vs. Professional: 75-85%

Critical areas:

  • Crawl spaces
  • Attics
  • Basements
  • Garage walls
  • Exterior walls
  • Under sinks (exterior walls)

Materials:

  • Foam pipe insulation sleeves
  • Heat tape or cable (for extremely cold areas)
  • Pipe wrap insulation

How to do it:

  • Measure pipes to determine insulation needed
  • Cut foam sleeves to length
  • Slip over pipes and seal seams with tape
  • Pay special attention to bends and joints
  • Insulate hot and cold water lines

When to hire a plumber:

  • Pipes need rerouting
  • Major plumbing modifications needed
  • Installing freeze-proof outdoor faucets

5. Replacing HVAC Filters

Difficulty: Very Easy
Time: 5-10 minutes
Cost: $10-$30 per filter
Frequency: Every 1-3 months

Why it matters: Clean filters improve efficiency, air quality, and prevent system breakdowns.

How to do it:

  • Turn off HVAC system
  • Locate filter (usually in return air duct or furnace)
  • Note filter size (written on frame)
  • Remove old filter
  • Insert new filter (check airflow direction arrow)
  • Turn system back on

Upgrade tip: Consider HEPA filters for better air quality, especially if you have allergies.

6. Testing Smoke and Carbon Monoxide Detectors

Difficulty: Very Easy
Time: 15-30 minutes
Cost: $15-$50 per detector
Importance: Life-saving

Winter risks: Increased furnace use, fireplace operation, and closed windows raise CO risks.

What to do:

  • Test all detectors monthly
  • Replace batteries annually (or when chirping)
  • Replace entire units every 10 years
  • Install CO detectors near bedrooms and on each floor
  • Ensure at least one smoke detector per floor

Never skip this step. Carbon monoxide is deadly and odorless.

7. Bleeding Radiators

Difficulty: Easy
Time: 30-60 minutes
Cost: $5 (radiator key)
Savings vs. Professional: 90%

If you have hot water radiators:

  • Air pockets reduce heating efficiency
  • Bleeding releases trapped air
  • Do this before heating season starts

How to do it:

  • Turn off heating system
  • Place towel and container under radiator valve
  • Insert radiator key into bleed valve
  • Turn counterclockwise until you hear hissing
  • When water starts dripping steadily, close valve
  • Repeat for each radiator
  • Turn heating system back on

8. Sealing Attic Bypasses

Difficulty: Moderate
Time: 4-8 hours
Cost: $50-$200
Savings: 10-20% on heating bills

Major heat loss areas:

  • Recessed lighting fixtures
  • Plumbing stack penetrations
  • Chimney chases
  • Attic hatches
  • Wire penetrations

Materials needed:

  • Expanding foam sealant
  • Weatherstripping
  • Rigid foam board
  • Caulk

Safety note: Ensure proper ventilation when using spray foam.

9. Storing and Draining Outdoor Equipment

Difficulty: Easy
Time: 1-2 hours
Cost: $0-$50

Garden hoses:

  • Disconnect and drain completely
  • Store coiled in garage or basement
  • Prevents bursting from freezing water

Sprinkler systems:

  • Blow out lines with compressed air
  • Or hire professional ($75-$150)

Outdoor faucets:

  • Turn off interior shutoff valves
  • Open exterior faucets to drain
  • Leave exterior faucets open all winter

Lawn equipment:

  • Drain gas from mowers, leaf blowers
  • Change oil
  • Clean and store in dry location
  • Consider winterizing service

10. Chimney and Fireplace Cleaning

DIY portion:

  • Remove ashes when cool
  • Clean glass doors
  • Check damper operation
  • Ensure clear airflow

Hire a professional chimney sweep for:

  • Creosote removal
  • Safety inspections
  • Chimney cap installation
  • Structural assessment
  • Wildlife removal

Cost: $150-$400
Frequency: Annually before use
Why: Prevents chimney fires and carbon monoxide buildup

When to Hire Professional Contractors

These winter prep tasks require licensed professionals:

1. HVAC System Inspection and Tune-Up

Always hire an HVAC technician.

Cost: $80-$200
Frequency: Annually before heating season
Best timing: September or October

What’s included:

  • Inspect heat exchanger for cracks
  • Check and clean burners
  • Test safety controls
  • Lubricate moving parts
  • Check thermostat accuracy
  • Measure airflow
  • Inspect electrical connections
  • Check gas pressure and connections
  • Test carbon monoxide levels
  • Clean condensate drain
  • Replace filters

Why professional service matters:

  • Prevents dangerous carbon monoxide leaks
  • Identifies problems before system fails
  • Maintains manufacturer warranty
  • Improves efficiency (saves 10-25% on heating)
  • Extends equipment life
  • Safety: gas furnaces require expertise

Red flags requiring immediate professional attention:

  • Yellow or flickering burner flame (should be blue)
  • Soot around furnace
  • Excessive rust or corrosion
  • Strange noises or odors
  • Frequent cycling on/off
  • Uneven heating

DIY mistake risks:

  • Gas leaks (explosion hazard)
  • Carbon monoxide poisoning
  • Fire hazards
  • Voided warranties
  • Equipment damage

2. Roof Inspection and Repairs

Hire a licensed roofer.

Cost: $200-$500 for inspection; repairs vary
Timing: Late summer or early fall
Frequency: Annually, especially after storms

What professionals check:

  • Shingle condition (cracks, curling, missing)
  • Flashing around chimneys and vents
  • Roof valleys
  • Soffit and fascia condition
  • Attic ventilation
  • Signs of leaks or water damage
  • Structural issues
  • Ice dam vulnerable areas

Why hire a pro:

  • Extremely dangerous (leading cause of construction deaths)
  • Requires expertise to identify subtle problems
  • Warranty on materials requires proper installation
  • Insurance may not cover DIY roof work
  • Proper safety equipment needed

Winter-specific concerns:

  • Ice dams from poor attic insulation/ventilation
  • Snow load capacity
  • Damaged shingles from summer storms
  • Clogged or damaged gutters

DIY risks:

  • Falls resulting in serious injury or death
  • Missing critical problems
  • Voiding roof warranty
  • Improper repairs causing more damage

3. Attic Insulation and Ventilation Upgrades

Hire an insulation contractor.

Cost: $1,500-$3,500 for average attic
ROI: Pays for itself in 2-5 years through energy savings
Ideal R-value: R-38 to R-60 depending on climate

Why professional installation:

  • Proper ventilation is critical (prevents ice dams)
  • Ensures even coverage
  • Identifies and seals air leaks
  • Proper vapor barrier installation
  • Safety concerns (asbestos, working in tight spaces)
  • Specialized equipment (blown-in insulation)

Signs you need more insulation:

  • Uneven room temperatures
  • Ice dams on roof
  • High heating bills
  • Can see joists in attic (insulation should cover them)
  • Cold floors on second story
  • Drafty rooms

Types of insulation:

  • Fiberglass batts (DIY-friendly but less efficient)
  • Blown-in cellulose (requires equipment)
  • Spray foam (requires professional application)

DIY risks:

  • Blocking ventilation (causes ice dams and mold)
  • Disturbing asbestos
  • Respiratory hazards
  • Electrical hazards
  • Inadequate coverage

4. Generator Installation

Always hire a licensed electrician.

Cost:

  • Portable generator: $400-$2,000 (DIY hookup risky)
  • Standby generator + installation: $3,000-$15,000

Why professional installation is essential:

  • Transfer switch required by code
  • Gas line installation (if needed)
  • Electrical permit required
  • Complex wiring
  • Safety critical

DIY risks:

  • Electrocution
  • Fire
  • Carbon monoxide poisoning (improper placement)
  • Back-feeding power to grid (can kill utility workers)
  • Code violations
  • Voided warranties

What professionals do:

  • Install proper transfer switch
  • Run gas lines safely
  • Ensure adequate ventilation
  • Meet all code requirements
  • Pull permits and pass inspections
  • Position unit correctly

Never use a portable generator without proper transfer switch.

5. Foundation Sealing and Waterproofing

Hire a foundation specialist.

Cost: $2,000-$10,000+ depending on extent
Timing: Before ground freezes
Importance: Prevents catastrophic damage

Why hire a pro:

  • Requires excavation equipment
  • Structural knowledge needed
  • Drainage systems must be properly designed
  • Serious consequences if done wrong

What they do:

  • Excavate around foundation
  • Apply waterproofing membrane
  • Install drainage tile/French drains
  • Repair foundation cracks
  • Grade soil away from foundation
  • Install sump pumps

Signs you need foundation work:

  • Water in basement
  • Cracks in foundation walls
  • Bowing or bulging walls
  • Wet crawl space
  • Musty odors
  • Efflorescence (white powder) on walls

Winter concerns:

  • Freeze-thaw cycles expand cracks
  • Ice can cause foundation movement
  • Wet soil freezes and expands

6. Gas Fireplace and Furnace Inspection

Hire certified technician.

Cost: $100-$250
Frequency: Annually
Timing: Before first use

What’s inspected:

  • Gas connections for leaks
  • Venting systems
  • Pilot lights and ignition
  • Safety controls
  • Carbon monoxide production
  • Flame color and pattern
  • Thermocouple operation

Why DIY is dangerous:

  • Gas leaks cause explosions
  • Improper venting causes CO poisoning
  • Fire hazards
  • Requires specialized knowledge

Warning signs:

  • Yellow or orange flames (should be blue)
  • Soot buildup
  • Pilot light won’t stay lit
  • Gas odor
  • No heat or inconsistent heating

7. Tree Trimming and Removal

Hire certified arborist.

Cost: $200-$2,000 per tree
Timing: Late fall after leaves drop
Safety: Extremely dangerous DIY

Winter tree risks:

  • Heavy snow and ice load
  • Dead branches falling
  • Trees falling on home during storms
  • Power line contact

What arborists do:

  • Remove dead or damaged branches
  • Identify diseased trees
  • Assess structural integrity
  • Safely remove hazardous trees
  • Have proper insurance
  • Use specialized equipment

Hire for:

  • Trees over 10 feet tall
  • Trees near power lines
  • Trees near structures
  • Dead or diseased trees
  • Storm-damaged trees

DIY risks:

  • Death or serious injury
  • Property damage
  • Power line contact (electrocution)
  • Damage to neighbor’s property

8. Ice Dam Prevention Systems

Hire specialized contractor.

Options and costs:

  • Heat cables: $300-$1,000 installed
  • Improved ventilation: $500-$2,000
  • Additional insulation: $1,500-$3,500
  • Metal roofing valleys: $1,000-$3,000

Professional solutions:

  • Install heat cables in valleys and edges
  • Improve attic insulation
  • Add or improve attic ventilation
  • Create ice-free pathways
  • Install water-tight underlayment

Why hire a pro:

  • Roof work is dangerous
  • Requires understanding of building science
  • Electrical work for heat cables
  • Proper ventilation design critical

Ice dam damage:

  • Roof leaks and interior damage
  • Damaged gutters
  • Ruined insulation
  • Mold growth
  • Structural damage

9. Boiler Maintenance and Repair

Hire licensed HVAC or plumber.

Cost: $150-$400 for annual service
Frequency: Annually before heating season

What’s included:

  • Check pressure and temperature
  • Inspect for leaks
  • Test safety valves
  • Clean heat exchanger
  • Check circulation pumps
  • Bleed radiators if needed
  • Test controls and thermostats

Why professional service:

  • Pressure vessels are dangerous
  • Gas or oil systems require expertise
  • Complex mechanical systems
  • Safety critical

Never DIY:

  • Pressure adjustments
  • Safety valve replacement
  • Gas line work
  • Major repairs

10. Window Replacement

Hire professional installers.

Cost: $300-$1,000 per window installed
Timing: Before winter (but can be done year-round)
ROI: 70-80% at resale; energy savings

Why professional installation:

  • Proper weatherproofing critical
  • Requires precise measurements
  • Heavy and awkward to handle
  • Warranty often requires professional install
  • Structural considerations

Energy-efficient upgrades:

  • Double or triple-pane glass
  • Low-E coatings
  • Argon or krypton gas fill
  • Insulated frames

Signs you need new windows:

  • Drafts even when closed
  • Condensation between panes
  • Difficulty opening/closing
  • Visible damage or rot
  • High energy bills

Month-by-Month Winter Prep Timeline

September

DIY Tasks:

  • Test heating system
  • Replace HVAC filters
  • Check weatherstripping

Hire Contractors:

  • Schedule HVAC tune-up
  • Schedule chimney sweep
  • Get roof inspection

October

DIY Tasks:

  • Clean gutters
  • Reverse ceiling fans
  • Seal air leaks
  • Store outdoor equipment

Hire Contractors:

  • Complete any roof repairs
  • Install storm windows
  • Foundation sealing (if needed)

November

DIY Tasks:

  • Insulate pipes
  • Drain outdoor faucets
  • Check smoke/CO detectors
  • Seal windows with plastic film (if needed)

Hire Contractors:

  • Generator installation (if planning)
  • Final tree trimming
  • Insulation upgrades

December-February

DIY Maintenance:

  • Change HVAC filters monthly
  • Remove snow from vents and exhaust
  • Keep gutters clear of ice
  • Monitor for ice dams

Call Contractors for:

  • Emergency HVAC repairs
  • Ice dam removal
  • Burst pipe repairs
  • Snow removal (if needed)

March

DIY Tasks:

  • Inspect for winter damage
  • Clean gutters of winter debris
  • Check basement for water intrusion

Hire Contractors:

  • Post-winter roof inspection
  • Repair any winter damage
  • Schedule spring maintenance

Emergency Winter Situations Requiring Immediate Professional Help

Call a contractor immediately if you experience:

Heating System Failure

  • Call: HVAC technician
  • Timeline: Same day/emergency service
  • Don’t: Try to repair gas furnace yourself
  • Do: Use space heaters safely while waiting (keep away from flammables)

Burst Pipes

  • Call: Emergency plumber
  • Timeline: Immediately
  • Do first: Shut off main water valve
  • Then: Open faucets to drain system
  • Document: Take photos for insurance

Roof Leak During Storm

  • Call: Roofing contractor
  • Timeline: ASAP (temporary fix, then permanent repair)
  • Emergency step: Place buckets, move valuables
  • Temporary: Tarps can prevent further damage

Carbon Monoxide Alarm

  • Call: 911, then HVAC/gas company
  • Timeline: Evacuate immediately
  • Never: Ignore or silence alarm
  • Danger: Can be fatal within minutes

Ice Dam Causing Interior Leaks

  • Call: Roofing contractor or ice dam specialist
  • Timeline: Within 24 hours
  • Don’t: Try to chip ice off roof yourself
  • Short-term: Place buckets, document damage

Gas Smell

  • Call: Gas company emergency line and 911
  • Timeline: Immediately evacuate
  • Don’t: Turn on/off lights or appliances
  • Don’t: Try to locate source yourself

Tree on House/Power Lines

  • Call: Emergency services, then insurance
  • Timeline: Immediately
  • Don’t: Touch anything or go near
  • Then: Tree removal and structural repairs

How to Choose Winter Preparation Contractors

HVAC Technicians

  • ✅ EPA certified (required for refrigerant)
  • ✅ Licensed and insured
  • ✅ Manufacturer certifications
  • ✅ Good reviews
  • ✅ Established local business
  • ✅ Clear pricing

Roofers

  • ✅ Licensed and bonded
  • ✅ Workers’ comp insurance
  • ✅ Manufacturer certifications
  • ✅ Local references
  • ✅ Written warranties
  • ✅ Proper safety equipment

Insulation Contractors

  • ✅ BPI or RESNET certified
  • ✅ Experience with your insulation type
  • ✅ Energy audit capability
  • ✅ Warranty on work
  • ✅ Proper ventilation knowledge

Electricians

  • ✅ Master or journeyman license
  • ✅ Insurance and bonding
  • ✅ Generator installation experience
  • ✅ Pull permits
  • ✅ Code compliance guarantee

Cost Breakdown: Professional Winter Preparation

Essential Professional Services:

  • HVAC tune-up: $150-$250
  • Chimney sweep: $150-$400
  • Roof inspection: $200-$500
  • Total: $500-$1,150

Recommended Professional Services:

  • Gutter cleaning (multi-story): $150-$350
  • Professional caulking: $200-$500
  • Insulation upgrade: $1,500-$3,500
  • Weatherization audit: $200-$500

Optional Upgrades:

  • Generator installation: $3,000-$15,000
  • New windows: $3,000-$10,000+
  • Ice dam prevention: $500-$3,000

Total investment: $500-$30,000+ depending on needs

ROI on Winter Preparation

Energy Savings:

  • Proper insulation: 10-30% on heating bills
  • HVAC tune-up: 10-25% on heating bills
  • Weatherstripping and caulking: 5-15% on energy costs
  • New windows: 10-25% on energy costs

Prevented Damage:

  • Burst pipe repair: $2,000-$10,000+
  • Ice dam damage: $5,000-$20,000+
  • Roof replacement from neglect: $5,000-$25,000+
  • HVAC replacement from poor maintenance: $3,000-$10,000+

The math is simple: Prevention costs less than repairs.

Winter Preparation Checklist

DIY Tasks (Cost: $100-$500)

  • ☐ Weather stripping and caulking
  • ☐ Gutter cleaning (single story)
  • ☐ Reverse ceiling fans
  • ☐ Insulate exposed pipes
  • ☐ Replace HVAC filters
  • ☐ Test smoke/CO detectors
  • ☐ Seal attic bypasses
  • ☐ Store outdoor equipment
  • ☐ Clean fireplace
  • ☐ Drain outdoor faucets

Professional Services (Cost: $500-$1,500)

  • ☐ HVAC tune-up and inspection
  • ☐ Chimney sweep and inspection
  • ☐ Roof inspection
  • ☐ Gutter cleaning (multi-story)
  • ☐ Gas fireplace inspection
  • ☐ Boiler maintenance

Major Upgrades (Cost: $1,000-$30,000+)

  • ☐ Insulation improvement
  • ☐ New windows
  • ☐ Generator installation
  • ☐ Ice dam prevention
  • ☐ Foundation waterproofing
  • ☐ HVAC replacement (if needed)

The Bottom Line

Winter preparation combines DIY efforts with professional expertise:

Handle yourself:

  • Weatherproofing
  • Basic maintenance
  • Simple insulation tasks
  • Equipment storage

Hire professionals for:

  • HVAC service
  • Roof work
  • Electrical projects
  • Gas systems
  • Structural issues
  • Safety-critical tasks

Don’t gamble with:

  • Your safety
  • Your family’s health (CO, fire hazards)
  • Your home’s structural integrity
  • Expensive equipment
  • Code compliance

The investment in professional winter preparation pays for itself through:

  • Lower energy bills
  • Prevented damage
  • Extended equipment life
  • Peace of mind
  • Safety assurance

Ready to Winterize Your Home?

Don’t wait until the first freeze to discover problems. Start your winter preparation now with help from qualified professionals.

Connect with local contractors for:

✅ HVAC technicians for furnace tune-ups
✅ Roofers for inspections and repairs
✅ Insulation contractors for energy upgrades
✅ Electricians for generator installation
✅ General contractors for comprehensive winterization

Get estimates from licensed, insured professionals in your area. Submit your project details and compare quotes from top-rated contractors near you.

Protect your home this winter—get started for free today.


Frequently Asked Questions

When should I start winterizing my home?

Start in early September for inspections and scheduling contractors. Complete all work by late November before harsh winter weather arrives. Some tasks (like insulation) are harder in winter but still possible.

How much does winter home preparation cost?

DIY tasks: $100-$500 in materials. Essential professional services: $500-$1,500. Major upgrades: $1,000-$30,000+. Most homeowners spend $800-$2,000 on winter prep, which pays for itself through energy savings and prevented damage.

Can I winterize my home myself?

Many tasks are DIY-friendly: weatherstripping, caulking, gutter cleaning (single-story), filter replacement, and basic maintenance. However, hire professionals for HVAC service, roof work, electrical projects, gas systems, and anything requiring permits.

What’s the most important winter preparation task?

HVAC inspection and tune-up. A failed furnace in winter is dangerous and expensive. Annual professional service prevents breakdowns, improves efficiency, and ensures safe operation. This one service can save you thousands in emergency repairs.

How can I prevent frozen pipes?

Insulate exposed pipes, seal air leaks, maintain 55°F minimum temperature, open cabinet doors during extreme cold, let faucets drip slightly, and drain outdoor faucets. For problem areas, install heat cable or call a plumber for permanent solutions.

Are ice dams dangerous?

Yes. Ice dams cause roof leaks, interior water damage, damaged gutters, ruined insulation, and mold growth. They indicate ventilation or insulation problems. Professional solutions include heat cables, improved attic insulation/ventilation, and proper roofing materials.

How often should I have my chimney cleaned?

Annually before use, or after burning one cord of wood. Professional chimney sweeps remove dangerous creosote buildup, inspect for damage, and ensure safe operation. Chimney fires are preventable with proper maintenance.

Do I really need a carbon monoxide detector?

Absolutely. CO poisoning kills hundreds annually and is completely preventable. Install CO detectors on every floor, especially near bedrooms. Test monthly, replace batteries annually, and replace units every 10 years. This is non-negotiable.

When should I replace my HVAC system?

If your system is 15-20 years old, requires frequent repairs, has uneven heating, causes high energy bills, or fails inspection, consider replacement. Modern systems are 30-50% more efficient and may qualify for tax credits.

Can winter prep increase my home’s value?

Yes. Energy-efficient upgrades (insulation, windows, HVAC), proper maintenance, and documentation of professional service increase resale value. New windows return 70-80%, insulation pays for itself in energy savings, and well-maintained homes sell faster.


Remember: Winter preparation isn’t optional—it’s essential home maintenance. The combination of DIY efforts and professional expertise keeps your home safe, comfortable, and efficient all winter long.