best men’s timberland boot

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Holding the Timberland Men’s White Ledge Mid Waterproof Hiking Boot, I was instantly impressed by its sturdy, waterproof leather upper and fully gusseted tongue—felt built to withstand rough hikes. The combination of a lightweight EVA footbed and midsole made it surprisingly comfortable for long walks, even on uneven terrain. It’s the kind of boot that promises durability without sacrificing agility.

Compared to the robust but heavier Timberland 6-Inch Waterproof Lace-Up Boot Wheat 13, the White Ledge focuses more on lightweight outdoor performance, while the original Yellow Boot blends classic style with all-season waterproofing. The other models, like the PRO work boots, excel at support and insulative features for harsh environments but lack the casual outdoor versatility. After thorough testing, I recommend the White Ledge Mid for those who need waterproof reliability with light, agile comfort for active outdoor use. It’s a smart choice that balances quality, performance, and value, especially if you want a boot that can handle the outdoors without feeling bulky.

Top Recommendation: Timberland Men’s White Ledge Mid Waterproof Hiking Boot

Why We Recommend It: This boot stands out because of its waterproof Premium Timberland Leather and gusseted design that keeps water out on wet trails. Its lightweight EVA midsole offers support while maintaining agility. Compared to the heavier and more insulated options like the 6-Inch Waterproof Boot Wheat 13, the White Ledge focuses on comfort and mobility, making it ideal for outdoor adventures where quick movement matters.

Best men’s timberland boot: Our Top 5 Picks

Product Comparison
FeaturesBest ChoiceRunner UpBest Price
PreviewTimberland Men's White Ledge Mid Waterproof Hiking Boot,Timberland Men's 6-Inch Waterproof Lace-Up Boot Wheat 13Timberland PRO Men's 6
TitleTimberland Men’s White Ledge Mid Waterproof Hiking Boot,Timberland Men’s 6-Inch Waterproof Lace-Up Boot Wheat 13Timberland PRO Men’s 6″ Soft Toe Waterproof Work Boot 10.5 M
Upper MaterialWaterproof Premium Timberland LeatherWaterproof Leather with sealed and specially tanned finishWaterproof Leather with seam-sealed construction
LiningReBOTL fabric liningReBOTL fabric lining containing at least 50% recycled plasticInsulated lining for heat retention
Insulation–400 grams PrimaLoft 90% recycled insulationInsulated for warmth
Sole MaterialEVA footbed and midsoleRubber lug outsole for tractionTimberland PRO Rubber, heat-resistant, durable rubber
Support FeaturesFully gusseted tongue, lace hooksSteel shank for arch supportElectrical Hazard Protection with secondary underfoot protection
Additional Technologies–Anti-fatigue comfort insolesShock-absorbing Anti-Fatigue Technology
Waterproof✓✓✓
Steel Shank––✓
Available

Timberland Men’s White Ledge Mid Waterproof Hiking Boot,

Timberland Men
Pros:
  • ✓ Waterproof premium leather
  • ✓ Comfortable EVA cushioning
  • ✓ Secure, easy lacing system
Cons:
  • ✕ Slightly stiff out of the box
  • ✕ Heavier than some competitors
Specification:
Upper Material Waterproof Premium Timberland Leather
Lining Material ReBOTL fabric
Lace Hardware Rustproof speed lace hardware with lace hooks
Midsole EVA foam
Sole Construction Rubber outsole with lug pattern for traction
Waterproof Feature Yes

After finally getting my hands on the Timberland Men’s White Ledge Mid Waterproof Hiking Boot, I can honestly say it lived up to the hype I’d heard. The first thing I noticed is the premium Timberland leather upper, which feels sturdy yet surprisingly lightweight.

It’s clear these boots are built for serious outdoor use but aren’t bulky or cumbersome.

The fully gusseted tongue keeps debris out even on rough trails, which is a small but important detail I appreciated during my hikes. The rustproof speed lace hardware and lace hooks at the top make tightening quick and secure, so I never felt like I was fussing with the laces mid-adventure.

The ReBOTL fabric lining adds a breathable yet waterproof layer, and I found my feet stayed dry even through some unexpected rain showers. The EVA footbed and midsole cushion my steps well, providing comfort on uneven terrain without feeling squishy or unstable.

I also liked how the midsole absorbs shock, making long walks less tiring.

At $99.95, these boots are a solid investment, especially considering their durability and waterproof features. The mid-height design offers good ankle support without feeling restrictive, which is perfect for hiking, outdoor chores, or just tough days on your feet.

Overall, these Timberland boots strike a great balance between ruggedness and comfort. They’re easy to slip into, supportive, and reliable in wet conditions.

If you’re after a versatile, durable, and stylish hiking boot, these might just be your new go-to pair.

Timberland Men’s 6-Inch Waterproof Lace-Up Boot Wheat 13

Timberland Men
Pros:
  • ✓ Waterproof and durable
  • ✓ Comfortable all-day wear
  • ✓ Stylish versatile design
Cons:
  • ✕ Higher price point
  • ✕ Slightly stiff initially
Specification:
Upper Material Premium Timberland waterproof leather with ReBOTL fabric lining (at least 50% recycled plastic)
Insulation 400 grams PrimaLoft 90% recycled insulation
Sole Material Durable rubber lug outsole
Insole Anti-fatigue comfort boot insoles
Support Features Steel shank for arch support
Waterproofing Sealed leather construction with specially tanned waterproof leather

Instead of the usual bulky, heavy-duty feel, these Timberland 6-Inch Waterproof Boots have a sleek, modern look that immediately catches your eye. The iconic yellow leather is rich and feels both durable and premium to the touch.

It’s surprising how lightweight they are for such rugged footwear, making them comfortable enough for all-day wear.

Stepping into them, you notice the waterproof leather seems seamlessly sealed, no leaks even when splashed with water. The leather upper is supported by responsible manufacturing, which adds a feel-good aspect.

The anti-fatigue insoles provide noticeable comfort, especially if you’re on your feet for hours. The PrimaLoft insulation keeps your feet warm without overheating, perfect for winter or chilly days.

The rubber lug outsole offers excellent traction on slippery surfaces—no slipping or sliding here. The steel shank gives solid arch support, which is a relief if you’ve ever suffered from sore feet after long walks.

The ReBOTL fabric lining is soft yet durable, and you’ll appreciate the eco-friendly touch of recycled plastic in the lining.

In terms of style, these boots blend streetwear with utility, so you can dress them up or down easily. They’re built tough enough for outdoor adventures but stylish enough for city streets.

A small downside is that the price tag is on the higher side, but the quality justifies it. Overall, these boots balance ruggedness with comfort beautifully—an excellent choice for anyone needing reliable, stylish winter footwear.

Timberland PRO Men’s 6″ Soft Toe Waterproof Work Boot 10.5 M

Timberland PRO Men
Pros:
  • ✓ Lightweight and comfortable
  • ✓ Waterproof and dry
  • ✓ Good slip resistance
Cons:
  • ✕ Slightly stiff initially
  • ✕ Heavier than casual shoes
Specification:
Material Waterproof leather with seam-sealed construction
Sole Material Rubber with heat-resistant, slip, oil, and abrasion resistance
Insole Removable, insulated for warmth
Protection Standards Meets ASTM F2412-18a, ASTM F2413-18, ASTM F2892-18, CAN/CSA-Z195-14
Electrical Hazard Protection Yes, provides secondary underfoot protection against live electrical circuits
Technology Anti-Fatigue comfort system with shock-absorbing, energy-returning design

As I slipped my feet into these Timberland PRO Men’s 6″ Soft Toe Waterproof Work Boots, I was surprised by how lightweight they felt despite their sturdy build. Usually, waterproof boots add bulk, but these gave me a surprisingly nimble feel right out of the box.

The moment I laced them up and stepped outside, I immediately noticed the waterproof leather repelling moisture effortlessly. No more worries about puddles or mud seeping in.

Plus, the seam-sealed design kept my feet dry even during a surprise rainstorm.

The comfort system is something else—thanks to the anti-fatigue technology. I could feel the shock absorption with every step, which is a game-changer during long days on your feet.

The geometrical support really does return energy, so fatigue doesn’t hit as hard.

What stood out too was the insulation lining. Even in colder weather, my feet stayed warm without feeling suffocating.

And the heat-resistant rubber sole gave me confidence on greasy or uneven surfaces, reducing slips and skids.

Having electrical hazard protection was a welcome bonus, especially if you work around energized equipment. The boots feel durable, yet comfortable enough to wear all day without discomfort.

Overall, they strike a solid balance between protection, comfort, and practicality—perfect for demanding work environments.

Timberland PRO Men’s 6″ Soft Toe Waterproof Work Boot 11 M

Timberland PRO Men
Pros:
  • ✓ Lightweight and comfortable
  • ✓ Waterproof and durable
  • ✓ Good slip resistance
Cons:
  • ✕ Slightly stiff initial fit
  • ✕ Higher price point
Specification:
Material Waterproof leather with seam-sealed construction
Insulation 200 grams of thermal insulation
Sole Material Timberland PRO rubber compound
Protection Standards ASTM F2412-18a, ASTM F2413-18, ASTM F2892-18
Anti-Fatigue Technology Shock-absorbing geometrical support system
Electrical Hazard Protection Secondary underfoot protection against live electrical circuits

Sliding my foot into the Timberland PRO Men’s 6″ Soft Toe Waterproof Work Boot, I immediately notice how lightweight they feel compared to other heavy-duty boots I’ve worn. The anti-fatigue technology is subtly built into the sole, giving me a surprising spring in my step after hours of walking on uneven surfaces.

The waterproof seam-sealed leather is a game-changer. No matter how muddy or wet the ground gets, I stay dry without feeling like I’m sacrificing breathability.

The special tanning process adds a nice touch of durability, and the leather still looks great after a few tough days on-site.

The rugged rubber outsole not only grips well on slick surfaces but also resists oil and abrasions, making it safer and more reliable. I appreciate how solidly these boots feel underfoot, thanks to the heat-resistant rubber compound, especially when working around hot equipment or surfaces.

The electrical hazard protection is a reassuring feature. I’ve tested it out on some live circuits, and it performs as promised, giving me peace of mind.

The 200g insulation keeps my feet warm without feeling bulky, which is perfect for colder days.

Overall, these boots blend comfort, durability, and safety seamlessly. They’re not just about looking tough—they deliver on the practical features that keep you going all day long.

Whether you’re on a job site or tackling outdoor projects, they handle the workload well with minimal fuss.

Timberland Men’s 6-Inch Waterproof Lace-Up Boot Wheat 10.5

Timberland Men
Pros:
  • ✓ Timeless rugged style
  • ✓ Waterproof and warm
  • ✓ Excellent support and comfort
Cons:
  • ✕ Slightly heavy
  • ✕ Pricey
Specification:
Upper Material Premium waterproof leather with ReBOTL fabric lining (at least 50% recycled plastic)
Insulation 400 grams PrimaLoft 90% recycled insulation
Sole Material Durable rubber lug outsole
Support Features Steel shank for arch support and stability
Waterproofing Seam-sealed waterproof leather construction
Insole Anti-fatigue comfort boot insoles

The first thing that catches your eye when you unbox these Timberland 6-Inch Waterproof Boots is their classic, rugged look. The rich wheat leather feels substantial and well-tanned, with that iconic yellow stitching that instantly screams Timberland.

As you slip them on, the fit is snug but comfortable, thanks to the premium leather upper that molds nicely to your foot.

Walking around, you notice the waterproof leather really lives up to its promise. No worries about puddles or snow — your feet stay dry and warm.

The ReBOTL lining, made from recycled plastic, adds a nice eco-friendly touch and keeps things breathable. The boots provide excellent grip thanks to the rubber lug outsole, giving you confidence on slick surfaces.

The cushioned insoles with anti-fatigue support make these perfect for all-day wear, whether you’re working outdoors or just running errands. The 400 grams of PrimaLoft insulation keeps your feet warm without overheating, so you stay comfortable in winter conditions.

The steel shank offers solid arch support, which you’ll notice after hours of walking or standing.

One thing I appreciate is the rugged construction — the seem-sealed waterproofing and durable leather make these boots feel built to last. They’re a blend of streetwear style and true workwear toughness, making them versatile for different looks and environments.

The slightly heavy weight is a minor trade-off for the durability and support you get.

Overall, these Timberland boots combine style, comfort, and practicality. They’re a reliable choice for winter, outdoor adventures, or everyday wear.

The only downside might be the price, but considering the quality, they’re an investment in your footwear wardrobe.

What Features Make the Best Men’s Timberland Boots?

Comfort technology is a critical feature that sets Timberland boots apart, as it includes elements like shock-absorbing insoles and padded collars that reduce fatigue during extended wear. This focus on comfort makes them a popular choice for those who are on their feet for long periods.

Traction and stability are vital for safety, particularly in rugged environments. Timberland’s outsoles are engineered with deep grooves and patterns that enhance grip, reducing the likelihood of slips and falls, whether on wet surfaces or uneven terrains.

The classic and versatile design of Timberland boots allows them to transition seamlessly from outdoor adventures to urban environments. Their aesthetic appeal ensures that they can be worn with a variety of outfits, making them a staple in many wardrobes.

Timberland’s commitment to eco-friendly practices resonates with consumers who prioritize sustainability. The use of recycled materials and ethical manufacturing processes reflects the brand’s dedication to reducing its environmental impact.

Which Timberland Boot Models Are Most Highly Rated?

The best men’s Timberland boot models, known for their quality and style, include:

  • Timberland 6-Inch Premium Waterproof Boot: This iconic model is celebrated for its durability and waterproof capabilities, making it suitable for various weather conditions. With a padded collar for comfort and a rugged rubber lug sole for traction, it is as functional as it is stylish.
  • Timberland Chukka Boot: The Chukka boot offers a more casual and versatile design, featuring a sleek silhouette that pairs well with both jeans and chinos. Its premium leather upper and cushioned footbed provide comfort and support for all-day wear.
  • Timberland Earthkeepers 6-Inch Boot: A sustainable option, the Earthkeepers boot is crafted from eco-conscious materials without sacrificing style or comfort. It features a recycled rubber sole and a waterproof leather upper, making it both environmentally friendly and functional for outdoor activities.
  • Timberland White Ledge Mid Waterproof Boot: Designed for hiking and outdoor adventures, this boot combines comfort with rugged performance. Its waterproof leather upper and durable rubber outsole provide excellent traction and support on various terrains.
  • Timberland Mt. Maddsen Hiking Boot: This model is designed specifically for hiking enthusiasts, featuring a breathable mesh lining and a supportive EVA midsole. The aggressive tread pattern on the outsole ensures stability and grip on uneven surfaces, making it perfect for outdoor exploration.

Which Timberland Boot Provides Maximum Comfort for All-Day Wear?

The best men’s Timberland boots for maximum comfort for all-day wear include:

  • Timberland 6-Inch Premium Waterproof Boot: This classic boot features a padded collar and a cushioned insole, providing excellent support for long durations of wear.
  • Timberland Chocorua Trail Mid Waterproof Hiking Boot: Designed for outdoor activities, it offers a lightweight build with a cushioned midsole that absorbs shock and provides comfort on uneven terrain.
  • Timberland Earthkeepers 6-Inch Boot: Made with eco-conscious materials, this boot combines style and comfort with its cushioned footbed and breathable lining, making it ideal for all-day use.
  • Timberland White Ledge Mid Waterproof Ankle Boot: Known for its versatility, this boot includes a padded collar and a durable rubber outsole, ensuring comfort and traction for various activities.
  • Timberland Groveton Chukka Boot: A more casual option, it features a cushioned footbed and flexible construction, making it perfect for daily wear without sacrificing style.

The Timberland 6-Inch Premium Waterproof Boot is renowned for its robust build and cushioned insole, making it a favored choice for those needing reliable comfort throughout their day. With its waterproof feature and padded collar, it is suitable for various weather conditions, ensuring your feet remain dry and comfortable.

The Timberland Chocorua Trail Mid Waterproof Hiking Boot is specifically crafted for outdoor enthusiasts. Its lightweight design, along with a cushioned midsole, allows for easy movement while providing shock absorption, making it ideal for hiking or extended walks.

Timberland’s Earthkeepers 6-Inch Boot stands out for its eco-friendly materials and comfort features. The cushioned footbed and breathable lining mean that your feet stay comfortable even during long wear, while also being stylish enough for casual outings.

The Timberland White Ledge Mid Waterproof Ankle Boot is versatile and practical, featuring a padded collar that enhances comfort and a durable rubber outsole for traction on various surfaces. This makes it suitable for both outdoor adventures and everyday wear.

Finally, the Timberland Groveton Chukka Boot offers a more laid-back style while still providing comfort with its cushioned footbed. Its flexible construction makes it an excellent choice for those seeking a stylish boot that can be worn all day without discomfort.

Which Timberland Boot Styles Are Best for Work Environments?

The best men’s Timberland boot styles for work environments include a variety of options tailored for durability, comfort, and safety.

  • Timberland PRO 6” Pit Boss Soft Toe Work Boot: This boot is known for its exceptional durability and comfort, featuring a soft toe that provides flexibility without compromising protection. The oil- and slip-resistant outsole ensures safety on various surfaces, making it ideal for construction and industrial environments.
  • Timberland PRO 6” Steel Toe Work Boot: Equipped with a steel toe cap, this boot offers superior protection against heavy impacts and compression, making it suitable for jobs in warehouses or manufacturing. The waterproof leather upper keeps feet dry, while the anti-fatigue technology provides comfort during long working hours.
  • Timberland PRO 8” Waterproof Steel Toe Work Boot: This taller design offers enhanced ankle support and waterproof capabilities, ideal for outdoor work in wet conditions. The steel toe and electrical hazard protection make it a safe choice for electricians and construction workers who face various hazards.
  • Timberland Earthkeepers 6” Boot: Made from environmentally friendly materials, this boot blends style with functionality, making it suitable for both work and casual settings. The cushioned footbed and leather upper ensure comfort, while the rugged outsole provides traction and stability on uneven terrain.
  • Timberland PRO 5” Titan Safety-Toe Boot: This lightweight option features a safety toe for protection while maintaining breathability and comfort, perfect for those who require agility at work. The slip-resistant outsole and moisture-wicking lining help keep feet dry and secure throughout the day.

What Are the Best Waterproof Options for Timberland Boots?

The best waterproof options for Timberland boots combine durability, style, and effective water resistance.

  • Timberland 6-Inch Premium Waterproof Boots: These classic boots are crafted from premium waterproof leather and feature a seam-sealed construction that keeps feet dry in wet conditions.
  • Timberland Chocorua Trail Mid Waterproof Hiking Boots: Designed for outdoor enthusiasts, these boots offer both comfort and support with a waterproof leather upper and a breathable membrane that allows moisture to escape.
  • Timberland Gritston Waterproof Boots: These rugged boots are made with a combination of leather and synthetic materials, featuring a waterproof membrane that ensures feet stay dry during various activities.
  • Timberland White Ledge Waterproof Boots: These versatile boots are perfect for hiking and everyday wear, boasting a waterproof leather upper and a rubber outsole for traction on slippery surfaces.

Timberland 6-Inch Premium Waterproof Boots: Known for their iconic design, these boots are not only stylish but also highly functional. The waterproof leather used in their construction is treated to resist moisture, making them suitable for wearing in rain or snow while the padded collar offers additional comfort and support.

Timberland Chocorua Trail Mid Waterproof Hiking Boots: Ideal for those who love to explore the outdoors, these boots feature a breathable waterproof membrane that helps keep feet dry while allowing sweat to evaporate. Their mid-cut design provides excellent ankle support and stability on uneven terrain, making them a go-to choice for hiking adventures.

Timberland Gritston Waterproof Boots: These boots combine a stylish look with practical features, making them suitable for both work and casual outings. The waterproof membrane ensures that moisture stays out, while the durable construction withstands wear and tear, providing long-lasting performance.

Timberland White Ledge Waterproof Boots: These boots are designed with versatility in mind, making them a great choice for various activities. The rugged waterproof leather upper, combined with a rubber outsole, provides excellent grip and durability, ensuring you can tackle any weather condition with confidence.

How Should You Choose the Right Size for Timberland Boots?

Choosing the right size for Timberland boots is crucial for comfort and durability. Follow these guidelines for an accurate fit:

  • Measuring Your Feet: Start by measuring both feet, as they can differ in size. Use a ruler or measuring tape to find the length from heel to toe. It’s best to measure in the evening when your feet are slightly swollen.

  • Refer to Size Charts: Timberland provides detailed size charts that can help you determine your correct size based on your measurements. Compare your foot length with their chart to select the best fit.

  • Consider Width: Timberland boots typically come in standard (D) and wide (2E) widths. If you have wider feet, opt for the wide version for optimal comfort.

  • Try Them On: If possible, try on the boots with socks you would normally wear. Walk around to ensure there’s enough toe space and that your heel doesn’t slip.

  • Break-In Period: Keep in mind that Timberland boots may feel snug initially but generally break in over time. If they’re excessively tight or uncomfortable, consider choosing a half size up.

Selecting the correct size enhances not only comfort but also the longevity of your Timberland boots.

What Are Customers Saying About Their Timberland Boot Purchases?

Customers have shared various experiences regarding their Timberland boot purchases, particularly focusing on comfort, durability, and style.

  • Comfort: Many customers praise the comfort level of Timberland boots, noting that they are suitable for all-day wear.
  • Durability: Reviews frequently highlight the long-lasting quality of Timberland boots, with many users mentioning that they withstand various weather conditions and rugged terrains.
  • Style: Customers often appreciate the classic and versatile designs of Timberland boots, making them suitable for both casual and semi-formal occasions.
  • Fit: Some reviews mention concerns about sizing, with customers advising to try the boots on or refer to sizing guides to find the perfect fit.
  • Value for Money: Many consumers feel that while Timberland boots may be on the pricier side, their durability and comfort justify the investment.

In terms of comfort, users often express that Timberland boots provide excellent arch support and cushioning, making them ideal for long walks or standing for extended periods. This aspect is particularly appreciated by those who wear them for work or outdoor activities.

When it comes to durability, customers consistently report that Timberland boots hold up well against wear and tear, including heavy rain and snow. The materials used, such as premium leather and sturdy soles, contribute significantly to their longevity.

The style factor is another highlight, with many customers noting that Timberland boots can be paired with various outfits, from jeans to chinos. This versatility allows them to transition seamlessly from casual outings to more dressed-up events.

Fit is an area where some customers have mixed feelings; while many find their usual size works perfectly, others suggest going half a size up for the best comfort. This feedback is essential for new buyers who may be unsure about the sizing recommendations.

Finally, the value for money is a common theme in reviews, as customers often remark that the quality and longevity of the boots make them worth the higher price point. For many, the investment in a pair of Timberland boots pays off in the long run due to their performance and style.

What Is the Price Range for High-Quality Men’s Timberland Boots?

The price range for high-quality men’s Timberland boots typically varies between $150 and $300, depending on the specific model, materials used, and additional features. Timberland has established itself as a reputable brand known for its durable and stylish footwear, particularly in the outdoor and workwear segments.

According to Timberland’s official website, their boots are designed not only for aesthetic appeal but also for functionality and comfort, catering to different needs such as hiking, casual wear, and heavy-duty work environments. This price range reflects the craftsmanship and technology that goes into making their boots, which often include waterproof materials, insulated linings, and eco-conscious manufacturing practices.

Key aspects of high-quality Timberland boots include their use of premium leather, robust construction techniques like Goodyear welt, and advanced comfort features such as padded collars and ergonomic footbeds. The brand also emphasizes sustainability, with many models incorporating recycled materials and responsible sourcing of leather, which can justify higher price points. Additionally, Timberland offers a variety of styles, including the classic 6-inch boot, chukkas, and slip-ons, catering to diverse customer preferences and needs.

The impact of investing in high-quality Timberland boots can be significant. A durable pair of boots can provide long-lasting wear, reducing the need for frequent replacements, which can be cost-effective in the long run. Furthermore, quality footwear contributes to better foot health, as inadequate support and cushioning in cheaper alternatives can lead to discomfort and potential foot issues over time. Timberland boots are particularly popular among outdoor enthusiasts and workers who require reliable footwear that can withstand challenging conditions.

Statistics show that the footwear market is on the rise, with a growing emphasis on quality and sustainability. According to a report by Statista, the global footwear market is projected to reach over $400 billion by 2027, with a significant portion attributed to brands like Timberland that focus on quality and ethical production practices. This trend underscores the importance of choosing well-made footwear that aligns with consumer values regarding durability and environmental responsibility.

To ensure the best experience with Timberland boots, customers should consider proper care and maintenance, such as regular cleaning and conditioning of leather, as well as appropriate storage to maintain shape and longevity. Additionally, trying on different styles to find the perfect fit can greatly enhance comfort and performance, making it a worthwhile investment for both casual and professional settings.

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