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Automated Bank Reconciliation Using Regex and AI | Tax Help Guy

Match transactions and reconcile accounts in minutes instead of hours

Published: November 15, 2025

"Automate bank reconciliation using regular expressions and AI language models. Match transactions, identify discrepancies, and reconcile accounts in minutes."

Tax Help Guy
Tax Help Guy
November 15, 2025

Automated Bank Reconciliation Using Regex and AI

Match transactions and reconcile accounts in minutes instead of hours

📅 Published: November 15, 2025⏱️ 15 min read

The Reconciliation Time Sink

Bank reconciliation is essential but time-consuming. Traditional reconciliation of 200 monthly transactions can take 4-6 hours. Bookkeepers must manually match each bank transaction to general ledger entries, identify discrepancies, and investigate variances.

With regex pattern matching and AI assistance, you can reduce this to 30-45 minutes while actually improving accuracy.

The Regex + AI Reconciliation Method

Phase 1: Data Preparation

Use regex to standardize both data sources:

// Bank statement cleaning 1. Extract amounts: \$[\d,]+\.\d{2} 2. Extract dates: \d{2}/\d{2}/\d{4} 3. Clean descriptions: Remove reference numbers, codes // General ledger cleaning 1. Standardize GL amount format 2. Normalize GL dates to same format 3. Extract check numbers: CHECK #(\d+)// Bank statement cleaning 1. Extract amounts: \$[\d,]+\.\d{2} 2. Extract dates: \d{2}/\d{2}/\d{4} 3. Clean descriptions: Remove reference numbers, codes // General ledger cleaning 1. Standardize GL amount format 2. Normalize GL dates to same format 3. Extract check numbers: CHECK #(\d+)

Phase 2: Exact Matching with Regex

Create composite keys for automatic matching:

Match Key Pattern: Date + Amount + First word of description Regex: (\d{4}-\d{2}-\d{2})\s+\$([\d,]+\.\d{2})\s+([A-Z]+) Example: Bank: "2025-11-15 $500.00 AMAZON PURCHASE" GL: "2025-11-15 $500.00 AMAZON" Match Key: "2025-11-15|500.00|AMAZON" Result: ✓ Exact MatchMatch Key Pattern: Date + Amount + First word of description Regex: (\d{4}-\d{2}-\d{2})\s+\$([\d,]+\.\d{2})\s+([A-Z]+) Example: Bank: "2025-11-15 $500.00 AMAZON PURCHASE" GL: "2025-11-15 $500.00 AMAZON" Match Key: "2025-11-15|500.00|AMAZON" Result: ✓ Exact Match

Phase 3: Fuzzy Matching with AI

For non-exact matches, use AI:

AI Fuzzy Matching Prompt:

"Match these bank transactions to GL entries: Bank: 2025-11-15 | $505.00 | AMAZON.COM*AB12 GL Options: A) 2025-11-15 | $500.00 | Amazon Office Supplies B) 2025-11-15 | $505.00 | Office Supplies C) 2025-11-16 | $505.00 | Amazon Which is the best match? Consider: - Amount matches exactly (B, C) - Date matches exactly (A, B) - Vendor name similarity Most likely match: B (same date, exact amount)"

























Identifying Unmatched Items

Bank Items Not in GL

After regex matching, remaining items are unmatched. AI Prompt: "These bank transactions have no GL entry: 1. 2025-11-10 | $45.00 | BANK FEE 2. 2025-11-15 | $1,200.00 | DEPOSIT XYZ CORP For each: - Suggest likely GL category - Identify if it's a missing entry or legitimate unrecorded item - Recommend correcting action"After regex matching, remaining items are unmatched. AI Prompt: "These bank transactions have no GL entry: 1. 2025-11-10 | $45.00 | BANK FEE 2. 2025-11-15 | $1,200.00 | DEPOSIT XYZ CORP For each: - Suggest likely GL category - Identify if it's a missing entry or legitimate unrecorded item - Recommend correcting action"

GL Items Not in Bank

GL entries without bank matches might be: - Checks not yet cleared (pattern: CHECK #\d+) - Pending deposits - Accruals (pattern: ACCRUAL|PREPAID) - Errors AI analyzes context to determine whichGL entries without bank matches might be: - Checks not yet cleared (pattern: CHECK #\d+) - Pending deposits - Accruals (pattern: ACCRUAL|PREPAID) - Errors AI analyzes context to determine which

Automated Reconciliation Workflow

  1. Extract bank data Use regex to pull date, amount, descriptionExtract bank data

    Use regex to pull date, amount, description

  2. Extract GL data Same fields from accounting systemExtract GL data

    Same fields from accounting system

  3. Standardize formats Regex patterns ensure apples-to-apples comparisonStandardize formats

    Regex patterns ensure apples-to-apples comparison

  4. Exact match (regex) ~70-80% match automaticallyExact match (regex)

    ~70-80% match automatically

  5. Fuzzy match (AI) ~15-20% matched with AI intelligenceFuzzy match (AI)

    ~15-20% matched with AI intelligence

  6. Flag exceptions (AI analysis) Remaining 5-10% flagged with explanationsFlag exceptions (AI analysis)

    Remaining 5-10% flagged with explanations

  7. Manual review Bookkeeper reviews only flagged itemsManual review

    Bookkeeper reviews only flagged items

Advanced Pattern Matching

Check Number Matching

Bank Pattern: CHECK #(\d+).*\$([\d,]+\.\d{2}) GL Pattern: Check (\d+).*\$([\d,]+\.\d{2}) Match if: - Check numbers identical (Group 1) - Amounts identical (Group 2) - Dates within 5 days (AI validates)Bank Pattern: CHECK #(\d+).*\$([\d,]+\.\d{2}) GL Pattern: Check (\d+).*\$([\d,]+\.\d{2}) Match if: - Check numbers identical (Group 1) - Amounts identical (Group 2) - Dates within 5 days (AI validates)

ACH/Wire Transfer Matching

Pattern: (ACH|WIRE|EFT)\s+([A-Z0-9]+) Extract transaction ID (Group 2) Match by ID + amount AI handles variations in descriptionPattern: (ACH|WIRE|EFT)\s+([A-Z0-9]+) Extract transaction ID (Group 2) Match by ID + amount AI handles variations in description

Discrepancy Analysis

Issue Regex Detection AI Resolution Timing difference Same amount, off by 1-3 days Analyze if reasonable delay Amount off by cents Pattern: within $0.10 Suggest rounding issue Missing transaction No regex match found Categorize as unrecorded Duplicate entry Exact pattern match 2x Verify if legitimateIssue Regex Detection AI ResolutionIssue Regex Detection AI ResolutionTiming difference Same amount, off by 1-3 days Analyze if reasonable delay Amount off by cents Pattern: within $0.10 Suggest rounding issue Missing transaction No regex match found Categorize as unrecorded Duplicate entry Exact pattern match 2x Verify if legitimateTiming difference Same amount, off by 1-3 days Analyze if reasonable delayAmount off by cents Pattern: within $0.10 Suggest rounding issueMissing transaction No regex match found Categorize as unrecordedDuplicate entry Exact pattern match 2x Verify if legitimate
IssueRegex DetectionAI Resolution
Timing differenceSame amount, off by 1-3 daysAnalyze if reasonable delay
Amount off by centsPattern: within $0.10Suggest rounding issue
Missing transactionNo regex match foundCategorize as unrecorded
Duplicate entryExact pattern match 2xVerify if legitimate

Time Savings Analysis

Task Manual Regex+AI Savings Match 200 transactions 4-6 hours 15-30 min 90% faster Find discrepancies 1-2 hours 5 min 95% faster Document variances 30 min 2 min 93% fasterTask Manual Regex+AI SavingsTask Manual Regex+AI SavingsMatch 200 transactions 4-6 hours 15-30 min 90% faster Find discrepancies 1-2 hours 5 min 95% faster Document variances 30 min 2 min 93% fasterMatch 200 transactions 4-6 hours 15-30 min 90% fasterFind discrepancies 1-2 hours 5 min 95% fasterDocument variances 30 min 2 min 93% faster
TaskManualRegex+AISavings
Match 200 transactions4-6 hours15-30 min90% faster
Find discrepancies1-2 hours5 min95% faster
Document variances30 min2 min93% faster

Professional Reconciliation Services

We use advanced automation to deliver same-day reconciliation services with exceptional accuracy.

Call (951) 203-9021

Conclusion

Bank reconciliation automation represents one of the highest-value applications of regex + AI in bookkeeping. By using regex for precise pattern matching and AI for contextual intelligence, bookkeepers can reduce reconciliation time by 90% while improving accuracy and catching issues that might be missed in manual review.

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Articles written by AI
curated by Joseph Stacy.

Anyone may arrange his affairs so that his taxes shall be as low as possible; he is not bound to choose that pattern which best pays the treasury. There is not even a patriotic duty to increase one's taxes. Over and over again the Courts have said that there is nothing sinister in so arranging affairs as to keep taxes as low as possible. Everyone does it, rich and poor alike and all do right, for nobody owes any public duty to pay more than the law demands.



Judge Learned Hand
Chief Judge of the United States Court of Appeals
for the Second Circuit
Gregory v. Helvering, 69 F
Judge Learned Hand

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