If I've never filed taxes and receive a 1099 from DoorDash will the IRS know?

Thanks for the clear explanation. I had a feeling that was the case! Two follow-up questions: 1) Is there a specific earnings threshold where DoorDash is required to send a 1099? 2) What happens if I earn less than that threshold - does the IRS still know about the income somehow?

For 2025 filing (2024 tax year), companies like DoorDash are required to issue a 1099-NEC when they pay you $600 or more during the year. This is the threshold that triggers their legal obligation to report to the IRS. If you earn less than $600 from DoorDash, they typically won't send a 1099-NEC to you or the IRS. However, you're still legally required to report all income earned, even if it's below the 1099 threshold. The IRS may not automatically "know" about income below the reporting threshold, but that doesn't exempt you from the requirement to report it.

Does it actually work for someone who's never filed taxes before? I'm in a similar situation with Instacart and have no clue where to even start. Does it like...walk you through the whole process or just tell you what you owe?

Sounds like an ad. How much does it cost? There's a ton of free tax info for gig workers online if you just google it.

It does work for first-time filers! It asks about your situation and then customizes everything. It walks you through the whole process, not just calculating what you owe. It explains each step, shows you which forms you need, identifies deductions specific to your delivery work, and even helps with quarterly estimated payments if you need those. The service isn't free, but for me it was worth it because I would have completely missed several deductions I was eligible for. They have different options depending on your needs, but I found the value was definitely there compared to potentially overpaying my taxes or dealing with IRS problems later.

How does that even work? The IRS phone system is such a nightmare, I don't understand how a third party service can get you through when calling directly fails.

Sounds too good to be true. The IRS is completely unreachable these days. I'll believe it when I see actual proof this works and isn't just taking people's money.

It works by using their system that continuously redials and navigates the IRS phone tree until it finds an opening in the queue. Once they secure a spot, they call you and connect you directly with the IRS agent who's about to pick up. It's like having someone wait on hold for you. I was skeptical too! But it's legit - they don't actually talk to the IRS for you or get any of your tax info. They just secure the phone connection and then bridge you directly to the IRS agent. I spent weeks trying to get through on my own with no success, and with this I was talking to a real person in less than 30 minutes.

What app do you use for tracking mileage? I've just been writing down my odometer readings in my notes app, but that seems inefficient.

I use Stride - it's free and you just hit "start drive" when you begin your dash and "end drive" when you finish. It uses GPS to track your route and calculate mileage. It also lets you log other expenses and estimates your tax bill based on your income and deductions. Everlance and Hurdlr are other popular options. Some have free versions with limited trips per month, but if you're delivering regularly, the paid versions are worth it and tax-deductible themselves. Much better than manual tracking, and if you ever get audited, you'll have detailed records with timestamps and maps.

This! I learned this the hard way. Made about $8000 driving last year, thought I was under the filing threshold, then got hit with a self-employment tax bill plus penalties for not filing. The self-employment tax threshold ($400) is much lower than the standard income tax filing threshold.

This is incredibly helpful information, thank you! I had no idea about the First Time Penalty Abatement - that could be a lifesaver for people in my situation who genuinely didn't know about the $400 self-employment tax threshold. One thing I'm still confused about though - when you mention deducting "phone data plan percentage used for work," how do you actually calculate that? Do you just estimate what percentage of your phone usage is for DoorDash, or is there a more official way to track it? I use my phone constantly for the app, GPS, and communicating with customers, but I also use it for personal stuff obviously. Same question for car maintenance - how do you prove to the IRS that oil changes or tire replacements were "related to delivery work" versus just normal car maintenance you'd do anyway? I'm trying to be thorough with record-keeping from the start, but I want to make sure I'm doing it right and not setting myself up for problems if I ever get audited.

Great questions about documentation! For phone usage, the IRS generally accepts reasonable estimates if you can justify them. I track my delivery hours and estimate about 70% of my phone usage during those hours is work-related (navigation, order management, customer calls). Keep a log for a few weeks to establish a baseline percentage, then apply that consistently. For car maintenance, the key is showing the business use percentage of your vehicle. If you drive 20,000 miles per year and 12,000 are for delivery work, you can deduct 60% of maintenance costs. Keep all receipts and maintain a mileage log that shows business vs personal use. The IRS accepts this method as long as your records are consistent and reasonable. Pro tip: Take photos of receipts and store them digitally. Create a simple spreadsheet with date, expense type, amount, and business percentage. This level of documentation will satisfy most IRS requirements and makes tax prep much easier. The standard mileage deduction (65.5 cents/mile for 2023) often covers most car expenses anyway, so you might not even need to itemize maintenance separately.

Great questions about documentation! For phone usage, the most defensible approach is to track your actual business usage. You can do this by noting hours spent on delivery apps, GPS navigation for work, and business-related calls/texts. Many drivers use a simple ratio - if you work 20 hours a week and use your phone 60 hours total, that's roughly 33% business use. Keep a log for a few weeks to establish your pattern. For car maintenance, the key is the business use percentage of your vehicle. If you drive 15,000 miles per year and 8,000 are for delivery work, then 53% of your maintenance costs are deductible. You don't need to prove each oil change was "for delivery work" - you just apply your business use percentage to all vehicle expenses. The IRS expects reasonable estimates based on actual records. Keep receipts, track your mileage religiously, and document your methodology. A simple spreadsheet noting total miles driven, business miles, and the percentage calculation will satisfy most auditors. The standard mileage deduction (65.5¢/mile for 2023) actually covers most vehicle expenses automatically, so many drivers find that simpler than tracking actual expenses.

Great questions about documentation! For phone expenses, the IRS accepts reasonable business use percentages. Most gig workers deduct 30-50% of their phone bill. You can track this by noting hours spent on delivery apps vs personal use, or keep a simple log for a few weeks to establish a pattern. The key is being consistent and reasonable - if you work 20 hours a week doing deliveries and use your phone 40 hours total, 50% is defensible. For car maintenance, you actually can't double-dip if you're using the standard mileage deduction (currently 65.5 cents/mile for 2023). The mileage rate already includes gas, maintenance, insurance, etc. You choose either actual expenses OR mileage deduction, not both. Most delivery drivers find the mileage method simpler and more beneficial. If you do choose actual expenses instead of mileage, you'd calculate the percentage of business use for your car (business miles divided by total miles) and apply that percentage to maintenance costs. But again, you can't use both methods in the same year. Keep receipts for everything and maintain a mileage log - even a simple spreadsheet with date, starting/ending odometer readings, and total miles works for IRS purposes.

Great questions about documentation! For phone expenses, the IRS allows reasonable allocation methods. I keep it simple - I track my work hours vs total phone usage hours in a month. If I work 20 hours a week doing delivery (80 hours/month) and use my phone about 200 hours total per month, that's roughly 40% business use. You can also look at data usage during work hours vs personal time if your carrier provides detailed usage reports. For car maintenance, the key is demonstrating the business purpose. I keep a simple log showing my total miles driven, business miles, and maintenance dates. If 60% of my driving is for delivery work, then 60% of maintenance costs are deductible. The IRS doesn't expect you to have separate oil changes for work vs personal - they understand cars are used for mixed purposes. Most importantly: keep receipts, maintain a mileage log, and document your methodology. If audited, consistency and reasonableness matter more than perfect precision. A simple spreadsheet showing your calculation method and supporting receipts will satisfy most IRS requirements. The standard mileage deduction (65.5 cents/mile for 2023) actually covers most car expenses anyway, so many drivers find it simpler than itemizing maintenance, gas, insurance, etc.

Great questions about documentation! For phone expenses, the most defensible approach is to track your work-related usage. You can estimate the percentage by looking at your delivery hours versus total phone usage time. For example, if you dash 20 hours a week and use your phone 60 hours total, you could reasonably deduct about 33% of your phone bill. Keep a log of your delivery hours to support this. Some drivers get a separate business line just for delivery work, which makes the deduction cleaner, but it's not required if you can reasonably allocate personal vs business use. For car maintenance, the key is showing the additional wear and tear from delivery work. Keep records of your total mileage, delivery mileage, and maintenance. If you drive 15,000 miles per year and 8,000 are for delivery, you could potentially deduct about 53% of maintenance costs. However, many tax professionals recommend just taking the standard mileage deduction (currently 65.5 cents per mile for 2023) instead of itemizing car expenses, as it's simpler and often results in a larger deduction anyway. The standard mileage rate is meant to cover gas, maintenance, insurance, and depreciation, so you can't double-dip by taking both mileage AND separate car expense deductions.

Great questions about documentation! For phone expenses, you can calculate the business percentage based on time spent using delivery apps versus total phone usage. Many drivers use around 20-30% as a reasonable estimate if they're doing delivery work regularly. Keep screenshots of your delivery app usage time from your phone's screen time settings as backup documentation. For car maintenance, the key is tracking your business mileage versus total mileage. If you drove 15,000 miles total last year and 8,000 were for delivery work, then roughly 53% of your car expenses could be business-related. Keep receipts for all maintenance and note the odometer reading and date. You don't need to prove each oil change was "because of" delivery work - the IRS accepts that business use of your vehicle creates proportional maintenance needs. Pro tip: Many tax pros recommend choosing either the standard mileage deduction (65.5 cents per mile for 2023) OR actual car expenses (gas, maintenance, insurance percentage, etc.), but not both. The mileage deduction is usually simpler and often more beneficial unless you have very high car expenses. Most importantly, keep everything organized from day one. A simple spreadsheet with dates, mileage, and expense categories will save you hours during tax season!

Great questions about documentation! For phone expenses, the IRS generally accepts reasonable business use percentages. I track mine by noting how many hours I'm actively delivering versus total phone usage. If I'm dashing 20 hours a week and use my phone 60 hours total, that's roughly 33% business use. Keep a log for a few weeks to establish your pattern. For car maintenance, the key is timing and mileage correlation. If you're putting on significantly more miles due to delivery work, maintenance becomes more frequent and can be partially deducted. I keep receipts for everything and note my delivery mileage percentage for the year. If 40% of my driving is for deliveries, I can deduct 40% of maintenance costs. The important thing is being able to show the IRS your reasoning if asked. Keep a simple spreadsheet with dates, services, costs, and your business use calculation. Photos of receipts stored in Google Drive or similar also help. Pro tip: the actual expense method for car deductions might be better than standard mileage if you have an older, high-maintenance vehicle with lots of delivery miles. Worth calculating both ways!

Great questions about documentation! For phone expenses, the IRS generally accepts a reasonable estimate based on your usage. I track mine by looking at my screen time data - on iPhone you can see app usage in Settings > Screen Time. I calculate what percentage DoorDash, GPS apps, and work-related calls/texts represent of my total usage. Most delivery drivers can reasonably claim 20-30% of their phone bill. For car maintenance, keep ALL your receipts and maintenance records. The key is using the business-use percentage of your vehicle. If you drive 15,000 miles total per year and 8,000 are for delivery work, then 53% of your maintenance costs are deductible (8,000/15,000). Oil changes, tire rotations, brake work - it all counts at that percentage. The IRS doesn't expect you to have separate "business tires" - they understand that delivery driving accelerates normal wear and tear. Just keep detailed mileage logs (using apps like Stride that others mentioned) and all maintenance receipts. If audited, you'll need to show your business vs. personal mileage ratio and that the expenses were ordinary and necessary for your work. Pro tip: take photos of receipts immediately and store them digitally. Paper receipts fade over time!

Great questions about documentation! For phone usage, the IRS generally accepts reasonable estimates based on actual business use. I keep a log for a typical week or month showing when I use my phone for delivery work (app time, GPS navigation, customer calls/texts) versus personal use, then apply that percentage to my annual phone bill. Some drivers use apps that track business vs personal usage automatically. For vehicle maintenance, the key is proportional deduction based on business mileage versus total mileage. If 40% of your annual miles are for delivery work, you can generally deduct 40% of maintenance costs. Keep receipts for oil changes, tire replacements, etc., and note your total mileage and business mileage for the year. The IRS understands that business driving accelerates wear and tear. Pro tip: Take photos of your odometer readings at the start and end of each tax year, and keep a simple spreadsheet with dates, starting/ending mileage for each work session, and total miles driven. This creates a clear paper trail if you're ever audited. Most tax software or services (like that TaxR.ai site others mentioned) can help calculate these percentages properly and ensure you're following IRS guidelines for deductions.

Great questions about documentation! For phone expenses, the IRS accepts reasonable estimates based on your usage patterns. I track mine by noting how many hours per week I'm actively dashing versus total phone use. For example, if I dash 15 hours/week and use my phone 50 hours/week total, that's about 30% business use. Keep records of your dashing schedule to support this. For car maintenance, the key is proportional deduction based on business miles versus total miles. If 40% of your annual mileage is for delivery work, you can deduct 40% of maintenance costs like oil changes, tire rotations, etc. The IRS doesn't require you to prove a specific oil change was "for delivery work" - they accept the business-use percentage method. Keep receipts for all maintenance, track your total miles and business miles, and calculate the percentage at year-end. A simple spreadsheet works fine. Also consider whether to use actual expense method vs. standard mileage rate (currently 67¢/mile for 2024) - you can't mix both methods in the same year, and standard mileage often works out better for newer vehicles. Most important: start tracking everything now, even if you're not sure it's deductible. Better to have records you don't need than miss out on legitimate deductions!

For phone usage, the simplest method is to calculate based on time - if you deliver 20 hours a week and use your phone 60 hours total per week, you can deduct 33% of your phone bill. Keep a log for a month to establish your pattern, then use that percentage consistently. The IRS accepts reasonable business-use percentages as long as you can support them. For car maintenance, you actually can't "double dip" - if you're using the standard mileage deduction (currently 65.5 cents per mile for 2023), that already includes maintenance, gas, insurance, and depreciation. You can't deduct actual car expenses on top of the mileage rate. However, if you choose to deduct actual expenses instead of mileage (which sometimes works out better for high-maintenance vehicles), then you'd track the business percentage of your total driving. So if 30% of your annual mileage is for delivery work, you can deduct 30% of your maintenance costs, insurance, gas, etc. Most delivery drivers find the standard mileage deduction simpler and more beneficial, but it's worth calculating both ways to see which gives you a bigger deduction. Just remember - pick one method and stick with it for the entire tax year!

Great questions about documentation! For phone usage, the IRS accepts reasonable estimates based on your work patterns. I track mine by noting how many hours per week I'm actively doing deliveries versus total phone usage. If I'm delivering 20 hours/week and use my phone 60 hours/week total, that's roughly 33% business use. Keep a log for a few weeks to establish your pattern, then apply that percentage to your monthly bill. For vehicle maintenance, the key is demonstrating the business purpose. I keep a simple spreadsheet tracking my delivery miles versus total miles driven. If 40% of my annual mileage is for delivery work, then I can reasonably deduct 40% of maintenance costs like oil changes, tire rotations, etc. Major repairs get trickier - you'd want to show the additional wear was due to business use. The IRS looks for "ordinary and necessary" business expenses with reasonable documentation. You don't need perfect precision, but you do need a logical method and records to support it. Taking photos of receipts and keeping a mileage log are your best friends here. Most importantly, be consistent with whatever method you choose!

Great questions about tracking business use percentages! For phone expenses, the IRS accepts reasonable estimates if you can document them. I keep a simple log for a few weeks each quarter showing when I use my phone for delivery work vs personal use, then apply that percentage for the whole period. Many drivers find it's around 30-40% business use when actively delivering. For car maintenance, you don't need to prove specific repairs were "delivery-related" - if you're using the standard mileage deduction (65.5¢/mile for 2023), maintenance is already included in that rate. You can't double-dip by claiming both mileage AND separate maintenance expenses. However, if you choose actual expense method instead of standard mileage, then you'd deduct the business percentage of ALL car expenses (gas, maintenance, insurance, etc.) based on business miles vs total miles driven. Most delivery drivers find standard mileage much simpler and often more beneficial. The key is consistency and documentation. Whatever method you choose, stick with it and keep good records. Apps like Stride can help track both mileage and expenses automatically, which creates a solid audit trail if needed.

Great questions about documentation! For phone usage, the IRS generally accepts reasonable business use percentages. You can track this by monitoring your usage during work hours versus personal time, or use a simple method like "if I deliver 20 hours/week and use my phone 60 hours/week total, that's roughly 33% business use." Keep a log for a few weeks to establish a pattern, then apply that percentage consistently. Some drivers use a separate phone or line just for delivery work to make this cleaner. For car maintenance, the key is that it's proportional to your business mileage versus total mileage. If you drive 20,000 miles per year and 8,000 are for delivery work, you can deduct 40% of maintenance costs. Keep receipts and note your odometer readings. You don't need to "prove" specific oil changes were for delivery work - the IRS understands that increased business driving accelerates maintenance needs. The actual/expense method for vehicle costs is more complex than the standard mileage rate (67¢/mile for 2024), so many drivers just use the mileage deduction since it's simpler and often results in a larger deduction anyway. But definitely keep those maintenance receipts regardless - you might want to compare methods to see which saves you more money!

For phone expenses, you can use either a time-based or usage-based method. The simplest approach is to estimate the percentage of time you use your phone for work versus personal use. If you dash 20 hours a week and use your phone personally another 20 hours, you could reasonably claim 50% of your phone bill. Keep a log for a typical week to establish this percentage. For car maintenance, the IRS allows you to use either the standard mileage rate (which covers all vehicle expenses including maintenance) OR actual expenses. If you choose actual expenses, you can deduct the business percentage of maintenance costs. So if 60% of your driving is for delivery work, you can deduct 60% of oil changes, tire replacements, etc. The key is documentation - keep receipts for everything and maintain a mileage log that shows business vs. personal miles. Most delivery drivers find the standard mileage rate easier since it's currently $0.655 per mile for 2023 and you don't need to track individual maintenance costs. Pro tip: You can't use both methods in the same year, so calculate which gives you a bigger deduction before choosing your approach!

Great questions about documentation! For phone expenses, the IRS generally accepts reasonable business use percentages. I track this by noting how many hours per week I'm actively driving/using delivery apps versus total phone usage. For example, if I drive 20 hours a week and use my phone about 60 hours total, that's roughly 33% business use. Keep a simple log for a few weeks to establish your pattern, then apply that percentage consistently. For car maintenance, the key is the business use percentage of your vehicle. If you drive 15,000 miles per year total and 8,000 of those are for delivery work, then 53% of your maintenance costs can be deducted. However, most drivers find it simpler to just use the standard mileage deduction (65.5 cents per mile for 2023) since it covers gas, maintenance, depreciation, etc. You can't double-dip - it's either mileage OR actual expenses, not both. Keep receipts for everything and maintain a simple spreadsheet with dates, mileage, and business purpose. The IRS wants to see that you're making reasonable, good-faith efforts to track legitimate business expenses. A consistent system with documentation beats perfect precision every time.

Great questions about documentation! For phone expenses, the most defensible approach is to track your work hours and estimate based on that. If you work 20 hours a week out of 168 total hours, that's roughly 12% of your phone usage for work. Keep records of your delivery schedule to support this calculation. Some people use separate apps or phone logs, but the time-based percentage method is widely accepted. For car maintenance, the key is the business use percentage of your vehicle. If you drive 15,000 miles per year and 8,000 are for delivery work, then 53% of your maintenance costs can be deducted. Keep detailed mileage logs and save all maintenance receipts with dates. The IRS looks for reasonable business connection - if your delivery work significantly increases your driving, the additional wear and tear is deductible. Pro tip: You can choose between deducting actual vehicle expenses (gas, maintenance, insurance percentage) OR the standard mileage rate (65.5 cents per mile for 2023), but not both. For most delivery drivers, the mileage rate ends up being more beneficial and much simpler to track. Just make sure you have solid mileage records with dates, starting/ending locations, and business purpose.

Great questions about documentation! For phone usage, the IRS doesn't require exact tracking, but you should have a reasonable method. Many drivers estimate based on hours worked - if you drive 20 hours/week and use your phone 40 hours/week total, that's roughly 50% business use. Keep records of your work schedule and phone bills. Some apps can track business vs personal usage too. For car maintenance, the key is connecting it to your business mileage. If you drove 15,000 miles total and 10,000 were for delivery work, you can deduct 67% of maintenance costs (10,000/15,000). Keep receipts and a simple log showing total miles vs business miles each month. The IRS accepts reasonable allocation methods as long as you're consistent and have documentation. Don't overthink it - just be able to explain your methodology and keep good records. Most audits focus on whether your deductions are reasonable for your income level, not perfect precision on every calculation.

Great questions about documentation! For phone expenses, the most defensible approach is to track your business usage. You can estimate based on time spent actively delivering (like if you dash 20 hours/week out of 60 total phone hours, that's roughly 33%). Some drivers keep a simple log of their delivery hours to support this. For car maintenance, the key is the business use percentage of your vehicle. If you drive 15,000 miles per year and 8,000 are for delivery work, then about 53% of your maintenance costs could be business-related. Keep receipts and note the odometer reading and business mileage percentage at the time of service. The IRS doesn't require you to separate oil changes into "business" vs "personal" - they recognize that business use accelerates normal wear and tear. Just apply your business use percentage to total maintenance costs. So if you spend $100 on an oil change and your car is 53% business use, you can deduct $53. Most importantly, keep detailed mileage logs (using apps like Stride makes this easier) because your business use percentage drives most of your vehicle-related deductions. The IRS wants to see contemporaneous records, not reconstructed estimates after the fact.