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Policy Government MattersTop 10 Best Estimated Tax Software of 2026
Top 10 estimated tax software ranking covers tools like TaxAct, FreeTaxUSA, and QuickBooks with pros, limits, and fit notes for filers.
How we ranked these tools
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Framework: Features 40% · Ease 30% · Value 30%
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TaxAct is the best estimated-tax fit when you want repeatable, penalty-aware quarterly estimates that carry cleanly into payment forms, whereas QuickBooks is the better alternative if your quarterly estimating must reconcile with your accounting data without spreadsheet duplication.
Editor’s top 3 picks
Three quick recommendations before you dive into the full comparison below — each one leads on a different dimension.
TaxAct
Underpayment penalty estimation updates as income or withholding inputs change within the estimated-tax workflow.
Best for: Fits when W-2 and self-employment income need repeatable quarterly estimates with penalty-aware iterations.
FreeTaxUSA
Editor pickFederal and state estimated payment voucher generation stays connected to the same estimate inputs.
Best for: Fits when individuals need quarterly estimated tax outputs with self-employment and underpayment visibility.
QuickBooks
Editor pickEstimated tax planning inherits figures from QuickBooks transactions, reducing mismatch between projections and books.
Best for: Fits when accounting data and quarterly estimated payments must reconcile without spreadsheet duplication.
Comparison Table
TaxAct
consumer taxTax filing software that supports estimated tax calculations and quarterly payment forms for individual filers.
Underpayment penalty estimation updates as income or withholding inputs change within the estimated-tax workflow.
TaxAct’s estimated-tax workflow centers on quarterly income projection, then turns that projection into payment schedules and voucher-ready outputs. The engine can model common offset patterns like withholding applied against estimated payments, and it supports self-employment tax projection for Schedule SE planning. Underpayment penalty estimators are included so iterations show how changes in income or withholding affect penalty outcomes.
A tradeoff appears in the level of customization for complex entity allocation or multi-activity income modeling, where heavier scenarios may require more manual reconciliation. It fits best when a filer has W-2 wages, 1099-NEC or self-employment income, and wants repeatable quarterly recalculation instead of a one-time annual estimate.
- +Generates payment voucher outputs aligned to federal estimated tax planning
- +Includes underpayment penalty estimators for iterative quarterly adjustments
- +Projects Schedule SE self-employment tax using forecasted activity inputs
- +Keeps federal and state estimated workflows linked to shared income inputs
- –Complex multi-activity or multi-entity allocations can require extra manual checks
- –Estimated-payment modeling is less suitable for unusual withholding structures
Sole proprietors
Schedule SE quarterly income projection
More accurate quarterly payment targets
W-2 plus 1099 earners
Withholding offset against estimated taxes
Lower underpayment risk
Show 1 more scenario
Freelance professionals
Quarterly recalculation from changing income
Fewer surprises at year-end
Re-runs quarterly projections when income updates and reflects changes in penalty estimates.
Best for: Fits when W-2 and self-employment income need repeatable quarterly estimates with penalty-aware iterations.
FreeTaxUSA
consumer taxOnline tax filing software that supports estimated tax forms and quarterly payment preparation.
Federal and state estimated payment voucher generation stays connected to the same estimate inputs.
FreeTaxUSA fits best when estimated tax planning needs repeatable calculations across multiple quarters and multiple income types. The estimate flow ties income, deductions, credits, and withholding inputs to outputs like federal 1040-ES totals and state quarterly payment amounts. Self-employment projections are handled inside the same planning session, so Schedule SE inputs feed the federal computation without splitting into separate tools. A due-date calendar engine helps align payments to the correct quarter.
A tradeoff is that automation depth stays focused on calculation and form outputs rather than workflow management for internal teams. The best fit is an individual or small business owner who recalculates estimates after receiving new 1099-NEC income totals or after changes in W-2 withholding. Users who need complex multi-entity governance controls or RBAC-style review paths will find limited admin coverage.
- +Quarterly estimate workflow outputs federal and state payment vouchers
- +Schedule SE inputs run inside the same estimate calculation session
- +Underpayment estimation logic supports Form 2210 style reconciliation
- +Due-date calendar reduces mistakes when payments shift by quarter
- –Limited admin controls for review, audit trails, or multi-user governance
- –Does not provide extensibility features like custom calculation modules
Self-employed individuals
Quarterly SE income estimate
More accurate quarterly payment amounts
1099 earners with W-2
Offset estimates using withholding
Lower underpayment risk
Show 2 more scenarios
Small business owners
Update estimates after new 1099 totals
Fewer surprises in payments
Re-running the estimate updates voucher totals for the remaining quarters.
Households with uneven income
Check underpayment exposure
Actionable penalty planning
Underpayment penalty estimators support planning around safe harbor style thresholds.
Best for: Fits when individuals need quarterly estimated tax outputs with self-employment and underpayment visibility.
QuickBooks
SMBSmall business accounting software with estimated quarterly tax calculations for self-employed and business users.
Estimated tax planning inherits figures from QuickBooks transactions, reducing mismatch between projections and books.
QuickBooks fits estimated tax workflows when bookkeeping and tax projections must stay aligned, because income and withholding inputs originate in the accounting data model instead of spreadsheets. The system can support quarterly schedules for estimated payment planning by using transaction-dated history, recurring entries, and reports tied to accounts receivable, accounts payable, and payroll. Estimated voucher outputs are strongest when the same quarter boundaries used in reports match the due-date calendar used for planning.
A key tradeoff is that QuickBooks does not function as a standalone estimated tax calculator with deep tax-law scenario modeling for every edge case. The best fit is an organization that already tracks self-employment or pass-through activity in QuickBooks and wants underpayment reconciliation style outputs to be based on the same numbers used for cashflow and bookkeeping reports.
- +Shares the same bookkeeping source data used for income reporting
- +Integrates payroll and contractor payments for withholding and income aggregation
- +Quarterly planning reports align with transaction-dated books
- +Supports recurring journal entries for estimate workflows
- –Edge-case penalty and safe harbor scenario logic is limited
- –Estimated payment voucher workflows require external steps for final filing
- –Quarterly accuracy depends on disciplined chart of accounts mapping
- –Some allocation forecasting needs manual adjustments
Self-employed bookkeepers
Quarterly planning from transaction history
Fewer projection-to-books mismatches
Freelance contractors
1099-NEC income aggregation
More complete income totals
Show 1 more scenario
Single-owner S-corp
W-2 withholding and estimate tracking
Better withholding offset modeling
Payroll withholding data can inform how much remains for quarterly payments planning.
Best for: Fits when accounting data and quarterly estimated payments must reconcile without spreadsheet duplication.
H&R Block
consumer taxTax software that includes estimated tax payment support for federal filing workflows.
H&R Block ties quarterly estimate assumptions to the same return preparation data set to reduce mismatch between projections and filed values.
H&R Block combines estimated tax planning with tax filing workflows that stay consistent from quarterly calculations through year-end return preparation. The estimated payment process includes due-date driven projections, withholding offset modeling, and 1040-ES style payment generation paths.
- +Quarterly estimate workflow aligns with year-end return inputs for fewer disconnects.
- +Withholding offset modeling reduces guesswork when W-2 wages change midyear.
- +Self-employment tax projection supports Schedule SE inputs within the same guidance flow.
- +Estimate due-date calendar engine structures payments around required timing.
- –Requires careful input hygiene so quarterly projections match later return data.
- –Pass-through quarterly forecasting is limited compared with specialized planning tools.
Best for: Fits when quarterly estimates need to stay synchronized with year-end return inputs across W-2 and self-employment data.
Avalara
enterpriseIndirect tax software for tax calculation, exemption management, return filing, and cross-border compliance.
Jurisdiction and nexus-aware estimated tax configuration that updates with tax content changes across filing cycles.
Avalara generates and manages estimated tax workflows with an emphasis on jurisdictional compliance and automated tax content updates. The product connects tax calculations to accounting and commerce data so quarterly estimate inputs stay aligned with source transactions.
- +Jurisdiction-focused configuration that keeps estimated calculations tied to registered nexus
- +Accounting and transaction integrations reduce manual re-entry of estimate inputs
- +Automation around tax rule updates supports ongoing compliance changes
- +Role-based access supports controlled setup and filing operations
- –Requires careful setup of jurisdiction mapping and entity filing context
- –Estimated tax planning coverage can depend on connected source data quality
- –Less direct for one-off personal estimating than tax-first calculators
- –API automation breadth requires implementation time for custom workflows
Best for: Fits when teams need jurisdiction-aware estimated tax workflows tied to accounting data and governed access.
TaxBandits
SMBBusiness tax filing software that supports estimated tax payments and related federal forms for businesses.
Quarterly output workflow that recalculates estimated payment planning from 1040-ES and Schedule SE inputs in one projection cycle.
TaxBandits fits teams and solo filers who want a quarter-by-quarter estimated tax workflow with paid voucher outputs and an adjustable projection basis. The system supports an estimated tax calculation engine tied to common federal and self-employment inputs, then generates worksheet-style results suitable for payment planning.
- +Quarterly estimated tax projections tied to configurable income and withholding inputs
- +1040-ES style voucher and worksheet output for payment planning
- +Schedule SE self-employment projection support for SECA planning
- +Scenario recalculation reduces repeated spreadsheet edits during the year
- –Limited guidance depth for complex multi-entity or multi-member LLC allocations
- –Requires careful input hygiene to avoid compounding errors across quarterly runs
- –Less granular automation around EFTPS batch preparation than payroll-first ecosystems
- –State quarterly nexus rule handling can be too manual for edge-case jurisdictions
Best for: Fits when estimated payments need consistent quarterly recalculation and voucher-ready outputs for federal and self-employment scenarios.
TaxSlayer Self-Employed
SMBOnline tax filing software that includes quarterly estimated tax support for self-employed filers.
Built-in quarterly estimated payment workflow that continuously carries self-employment projection inputs into Form 1040-ES vouchers and underpayment reconciliation.
TaxSlayer Self-Employed targets quarterly estimated tax workflows for nonemployee income and includes a guided path for projecting Schedule SE self-employment tax. The software groups inputs around 1099-NEC totals, expense categories, and projected income so the Form 1040-ES generator can produce payment amounts and vouchers.
- +Quarterly projection flow ties self-employment income to Form 1040-ES voucher amounts
- +Schedule SE projection is integrated with income and deduction inputs instead of separate worksheets
- +W-2 withholding offset handling reduces manual reconciliation steps
- +Estimated payment due-date guidance helps avoid missed quarterly cycles
- –Requires disciplined input updates each quarter to keep projections from drifting
- –Limited visibility into edge-case penalty logic details during underpayment estimator review
- –State estimated payment configuration can add manual steps for less common filing situations
- –Pass-through and multi-entity allocation support is less granular than some competitor tax suites
Best for: Fits when self-employed taxpayers need guided quarterly estimates that update cleanly into vouchers and reconciliation.
Vertex
enterpriseEnterprise tax technology for sales tax, use tax, VAT, and industry-specific compliance workflows.
Jurisdiction-aware estimated tax configuration that standardizes quarterly calculation and output generation across cases.
Vertex provides an estimated tax workflow centered on tax calculation configuration and output generation for individuals and businesses. It handles recurring quarterly estimated payment cycles with engines for federal and state computations and modeled offsets.
- +Configuration-first design for recurring quarterly estimated tax calculations
- +Federal and state computation support in a single estimated tax workflow
- +Modeling of withholding offsets to reconcile payment needs
- +Output artifacts fit payment voucher and filing submission workflows
- –Estimated tax setup requires more upfront configuration than consumer tools
- –User experience depends on admin-curated templates and jurisdiction rules
Best for: Fits when organizations need consistent quarterly estimated tax outputs across multiple jurisdictions and filer types.
Stripe Tax
API-firstAutomated tax calculation for online payments with support for sales tax, VAT, and GST.
Stripe Tax API determines tax amounts during payment authorization using transaction and address inputs.
Stripe Tax calculates sales and use tax by jurisdiction during checkout, using Stripe’s transaction data rather than separate tax forms. It is distinct for API-first integration with Stripe Payments and for applying tax automatically at the line-item level.
- +Line-item tax calculation runs from Stripe order data via API
- +Jurisdiction-based tax determination is embedded in checkout flows
- +Automatic tax totals reduce reconciliation against payment amounts
- +Webhooks provide tax result updates for downstream bookkeeping
- –Not built for federal quarterly estimated payments like Form 1040-ES
- –Tax behavior depends on correct product, address, and event data setup
- –Limited support for tax projection workflows such as underpayment Form 2210 reconciliation
- –State quarterly estimated payment nexus rules require separate tax logic elsewhere
Best for: Fits when sales tax must be computed automatically in Stripe checkout for ecommerce or marketplaces.
TaxJar
SMBSales tax software with automated calculation, filing support, and nexus tracking for online sellers.
Transaction-level capture feeding estimated payment forecasts across multiple state obligations, with automation hooks for recurring runs.
TaxJar is a specialized estimated tax workflow tool aimed at e-commerce and multi-channel sellers. It pairs sales and income reporting inputs with automated tax calculations and filing-ready outputs for federal and state obligations.
- +Commerce transaction imports reduce manual quarterly income aggregation
- +Rules-based outputs support estimated payment planning across states
- +Export formats fit common accounting and reconciliation workflows
- +API-oriented data access supports automation around tax inputs
- –Estimated income projections depend heavily on correct source data mapping
- –Complex pass-through allocation and multi-member modeling can require manual adjustments
- –Penalty and safe harbor analysis is less detailed than dedicated tax prep engines
- –State quarterly nexus nuances may need extra configuration effort
Best for: Fits when sellers need quarterly estimated planning built from commerce transaction data and state rules.
Conclusion
After evaluating 10 estimated tax software, TaxAct stands out as our overall top pick — it scored highest across our combined criteria of features, ease of use, and value, which is why it sits at #1 in the rankings above.
Use the comparison table and detailed reviews above to validate the fit against your own requirements before committing to a tool.
How to Choose the Right Estimated Tax Software
The selection cards in this guide also include QuickBooks, H&R Block, Avalara, TaxBandits, Vertex, Stripe Tax, and TaxJar to show where estimated tax calculation engines meet accounting sources, jurisdiction configuration, and automation surfaces. TaxAct stands out for underpayment penalty estimation updates as estimated-tax inputs change inside the same workflow, while FreeTaxUSA emphasizes connected federal and state voucher generation tied to the same estimate inputs.
Estimated Tax Software for quarterly calculation, voucher output, and underpayment reconciliation
FreeTaxUSA stays tightly coupled by generating federal and state estimated payment vouchers from the same estimate inputs while running Schedule SE inputs inside the same session. Other tools illustrate adjacent integration models, such as QuickBooks inheriting quarterly planning figures from bookkeeping transactions and TaxSlayer Self-Employed carrying self-employment projection inputs into Form 1040-ES vouchers and the underpayment reconciliation workflow.
Estimated tax workflow coverage, voucher output, and penalty-aware reconciliation
Estimated tax software earns its place when the quarterly calculation engine feeds the same session that produces federal and state voucher outputs and underpayment reconciliation. That continuity reduces mismatches that happen when estimates live in one worksheet and vouchers get rebuilt later.
Penalty-aware underpayment iteration inside the estimate workflow
TaxAct updates underpayment penalty estimation as estimated-tax inputs change within the same estimated-tax workflow, which supports iterative quarterly adjustments. TaxSlayer Self-Employed ties self-employment projections into Form 1040-ES vouchers and underpayment reconciliation as a continuous quarterly projection flow.
Connected federal and state voucher generation from one estimate session
FreeTaxUSA keeps federal and state estimated payment voucher generation connected to the same estimate inputs while running Schedule SE inputs inside the same session. H&R Block ties the quarterly estimate assumptions to the same return preparation dataset to reduce disconnects between projections and filed values.
Accounting-source integration to reduce re-entry between books and estimates
QuickBooks inherits estimated tax planning figures from QuickBooks transactions so quarterly projections reconcile without spreadsheet duplication. Avalara reduces manual re-entry by tying estimated calculations to registered nexus configuration plus accounting and transaction integrations.
Self-employment projection carry-through into Form 1040-ES vouchers
TaxSlayer Self-Employed carries self-employment projection inputs into Form 1040-ES vouchers and underpayment reconciliation inside its built-in quarterly estimated payment workflow. TaxBandits recalculates estimated payment planning from 1040-ES and Schedule SE inputs in one projection cycle for federal and self-employment scenarios.
Jurisdiction configuration for recurring quarterly outputs across filing contexts
Avalara uses jurisdiction and nexus-aware estimated tax configuration that updates with filing cycle tax content changes. Vertex provides configuration-first quarterly estimated tax calculations that support federal and state computation in a single estimated tax workflow.
Automation surfaces for commerce or payment-driven tax engines
Stripe Tax computes tax amounts during payment authorization using the transaction and address inputs via an API flow embedded in checkout. TaxJar captures commerce transaction inputs to feed estimated payment forecasts across state obligations with automation hooks for recurring runs.
Choose based on input source, jurisdiction complexity, and how vouchers get finalized
The fastest path to the right estimated tax software is matching the workflow shape to the source of truth for income and withholding. Tools vary mainly in whether estimated-tax inputs and voucher outputs stay connected, and whether jurisdiction logic is configuration-first or derived from consumer inputs.
Map the quarterly inputs to the tool’s calculation session
Select TaxAct if quarterly edits must update underpayment penalty estimation while estimates change inside the same workflow. Select FreeTaxUSA if federal and state estimated payment vouchers must stay connected to one estimate input session with Schedule SE run inside the same session.
Decide whether books should flow into estimates automatically
Choose QuickBooks when estimated tax planning must inherit figures from QuickBooks transactions so projections reconcile against the bookkeeping source. Choose Avalara when accounting and transaction integrations must reduce manual re-entry and the tool must apply jurisdiction and nexus-aware configuration.
Match self-employment workflows to voucher and reconciliation continuity
Choose TaxSlayer Self-Employed when self-employment projection inputs should flow directly into Form 1040-ES voucher amounts and underpayment reconciliation in a guided quarterly workflow. Choose TaxBandits when 1040-ES style voucher and worksheet outputs must be ready after a single recalculation cycle driven by 1040-ES and Schedule SE inputs.
Pick a jurisdiction model that fits the number of states and entities
Choose Avalara or Vertex when jurisdiction-aware configuration must standardize recurring quarterly outputs across cases. Choose consumer-focused tools like H&R Block when quarterly estimates must stay synchronized with return preparation inputs to reduce disconnects.
Use commerce or payment-tax APIs only when the use case matches
Choose Stripe Tax when the tax computation target is sales tax during payment authorization in checkout flows. Choose TaxJar when the planning target is state obligation forecasts built from commerce transaction imports with rules-based outputs.
Check governance and audit needs for multi-user or multi-entity planning
If governance controls matter for review and multi-user workflows, prefer tools with stronger administration and access patterns such as Avalara or Vertex. If the need is personal quarterly planning with voucher outputs tied to input updates, FreeTaxUSA provides connected voucher generation but offers limited admin controls.
Who should buy Estimated Tax Software for quarterly planning and voucher output
Estimated tax software fits readers who must produce quarterly payment amounts and vouchers while keeping penalty exposure and reconciliation aligned to changing inputs. Buyers also include operations teams that want transaction data to drive recurring forecasts instead of manual aggregation.
W-2 employees plus self-employed income who repeat quarterly estimates
TaxAct fits when quarterly estimates need underpayment penalty estimation to update as inputs change while producing federal voucher outputs aligned to iterative planning. FreeTaxUSA fits when quarterly outputs must generate both federal and state vouchers while running Schedule SE in the same estimate session.
Freelancers and sole proprietors running guided self-employment projections
TaxSlayer Self-Employed fits when quarterly self-employment projection inputs must carry through into Form 1040-ES vouchers and underpayment reconciliation. TaxBandits fits when a single projection cycle must recalculate from 1040-ES and Schedule SE inputs and output voucher-ready worksheets.
Owners who want bookkeeping-to-estimates consistency without spreadsheet duplication
QuickBooks fits when quarterly estimated tax planning must inherit figures from QuickBooks transactions so projections reconcile against books. H&R Block fits when quarterly estimate assumptions must stay synchronized with year-end return preparation data to reduce disconnects.
Teams that manage jurisdiction and nexus complexity across filing contexts
Avalara fits when jurisdiction and nexus-aware estimated tax configuration must update with tax content changes across filing cycles and tie to accounting and transaction integrations. Vertex fits when configuration-first recurring quarterly outputs must support federal and state computation across multiple jurisdictions and filer types.
Sellers and marketplaces that plan state obligations from commerce transactions
TaxJar fits when commerce transaction imports must reduce manual quarterly income aggregation and produce rules-based estimated payment planning across states. Stripe Tax fits only when the tax computation target is embedded in checkout payment authorization rather than federal quarterly estimated payments.
Common ways estimated tax workflows break and how to prevent them
Estimated tax software failures usually trace to input drift across quarters or to a voucher workflow that depends on manual transfer. The results show up as mismatched projections and underpayment exposure that does not reflect the final withholding and income picture.
Updating quarterly inputs but leaving vouchers based on stale estimate outputs
Use TaxAct when edits within the estimated-tax workflow update underpayment penalty estimation and keep iterative quarterly adjustments consistent. Use FreeTaxUSA when federal and state voucher generation stays connected to the same estimate inputs.
Assuming edge-case penalty logic is fully transparent during underpayment reconciliation
TaxSlayer Self-Employed provides guided quarterly updates into vouchers and underpayment reconciliation but shows limited visibility into edge-case penalty logic details during underpayment estimator review. TaxAct provides underpayment penalty estimation updates as inputs change, which supports iterative validation when behavior matters.
Choosing an accounting or jurisdiction integration tool without verifying data quality in the source systems
Avalara and TaxJar both depend on connected source data quality because accounting and transaction integrations drive estimate inputs and income projections. QuickBooks reduces mismatch by inheriting planning figures from bookkeeping transactions, but complex withholding structures may still require extra manual checks in edge cases.
Using a sales-tax or checkout tax engine for federal quarterly estimated payment planning
Stripe Tax is designed for tax amounts during payment authorization via API with transaction and address inputs, so it does not cover federal quarterly Form 1040-ES workflows. TaxJar supports estimated payment planning across states from commerce transactions, but it is not a direct substitute for Form 1040-ES voucher generation.
Proceeding with multi-entity allocation complexity without a plan for review and reconciliation
TaxAct can require extra manual checks when complex multi-activity or multi-entity allocations affect estimated-payment modeling. TaxBandits has limited guidance depth for complex multi-entity or multi-member LLC allocations, so input hygiene must be treated as a recurring control.
How We Selected and Ranked These Tools
We evaluated TaxAct, FreeTaxUSA, QuickBooks, H&R Block, Avalara, TaxBandits, TaxSlayer Self-Employed, Vertex, Stripe Tax, and TaxJar against estimated tax workflow coverage, voucher output continuity, and underpayment reconciliation support. Features drove 40% of the scoring, and ease and value each contributed 30% through how directly the quarterly estimate process produces voucher-ready outputs and keeps projections aligned.
TaxAct set the ranking standard because underpayment penalty estimation updates as income or withholding inputs change within the estimated-tax workflow. FreeTaxUSA ranked near the top because federal and state estimated payment voucher generation stays connected to the same estimate inputs while Schedule SE inputs run in the same estimate session.
Frequently Asked Questions About Estimated Tax Software
How do TaxAct and FreeTaxUSA keep quarterly federal estimate inputs consistent across repeated runs?
Which tools provide Schedule SE self-employment tax projection that feeds directly into estimated payment vouchers?
When does underpayment penalty exposure update in TaxAct compared with FreeTaxUSA?
Where does H&R Block handle reconciliation between quarterly estimates and year-end return data more tightly?
How does Avalara implement jurisdiction and nexus-aware configuration for quarterly estimated tax workflows?
Which platform fits teams that need audit history and governed access for estimated tax calculations?
How can data migration and workflow continuity be handled when switching from spreadsheets to an estimated tax tool?
What breaks if estimated tax calculations use mismatched source data between accounting systems and tax estimates in QuickBooks?
How do Vertex and TaxBandits differ in how users configure and recalculate quarter-by-quarter estimates?
Tools reviewed
Primary sources checked during evaluation.
Referenced in the comparison table and product reviews above.
Funding and competing interests
This study was co-funded by several of the vendors assessed in it. No single vendor funded it. Funders could propose the market studied.
They had no role in selecting vendors, setting or weighting criteria, analysing data or drawing conclusions, and they received the same factual-accuracy check as every other vendor assessed.
Market definition, inclusion rules and criteria weights were fixed by an editor before research began and did not change afterwards. Editorial process →
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