The repository is at github.com/sebastianspicker/AI-PDF-Renamer.

The Problem

Every PDF acquisition pipeline eventually produces the same chaos. Journal articles downloaded from publisher sites arrive as 513194-008.pdf or 1-s2.0-S0360131520302700-main.pdf. Scanned letters from the tax authority arrive as scan0023.pdf. Invoices arrive as Rechnung.pdf — every invoice from every vendor, overwriting each other if you are not paying attention. The actual content is in the file. The filename tells you nothing.

The human solution is trivial: open the PDF, glance at the title or date or sender, type a descriptive name. Thirty seconds per file, multiplied by several hundred files accumulated over a year, becomes a task that perpetually does not get done.

The automated solution sounds equally trivial: read the text, decide what the document is, generate a filename. What could be involved?

Quite a bit, it turns out. Working through the implementation is a useful way to make concrete some things about LLMs and text processing that are easy to understand in the abstract but clearer with a specific task in front of you.

Step One: Getting Text Out of a PDF

A PDF is not a text file. It is a binary format designed for page layout and print fidelity — it encodes character positions, fonts, and rendering instructions, not a linear stream of prose. The text in a PDF has to be extracted by a parser that reassembles it from the position data.

For PDFs with embedded text (most modern documents), this works well enough. For scanned PDFs — images of pages, with no embedded text at all — you need OCR as a fallback. The pipeline handles both: native extraction first, OCR if the text yield is below a useful threshold.

The result is a string. Already there are failure modes: two-column layouts produce interleaved text if the parser reads left-to-right across both columns simultaneously; footnotes appear in the middle of sentences; tables produce gibberish unless the parser handles them specifically. These are not catastrophic — for renaming purposes, the first paragraph and the document header are usually enough, and those are less likely to be badly formatted than the body. But they are real, and they mean that the text passed to the next stage is not always clean.

Step Two: The Token Budget

Once you have a string representing the document’s text, you cannot simply pass all of it to a language model. Two reasons: context windows have hard limits, and — even when they are large enough — filling them with the full text of a thirty-page document is wasteful for a task that only needs the title, date, and category.

Language models do not process characters. They process tokens — subword units produced by the same BPE compression scheme I described in the strawberry post. A rough practical rule for English text is:

$$N_{\text{tokens}} \;\approx\; \frac{N_{\text{chars}}}{4}$$

This is an approximation — technical text, non-English content, and code tokenise differently — but it is useful for budgeting. A ten-page academic paper might contain around 30,000 characters, which is approximately 7,500 tokens. The context window of a small local model (the default here is qwen2.5:3b via Ollama) is typically in the range of 8,000–32,000 tokens, depending on the version and configuration. You have room — but not unlimited room, and the LLM also needs space for the prompt itself and the response.

The tool defaults to 28,000 tokens of extracted text (DEFAULT_MAX_CONTENT_TOKENS), leaving comfortable headroom for the prompt and response in most configurations. For documents that exceed this, the extraction is truncated — typically to the first N characters, on the reasonable assumption that titles, dates, and document types appear early.

This truncation is a design decision, not a limitation to be apologised for. For the renaming task, the first two pages of a document contain everything the filename needs. A strategy that extracts the first page plus the last page (which often has a date, a signature, or a reference number) would work for some document types. The current implementation keeps it simple: take the front, stay within budget.

Step Three: Heuristics First

Here is something that improves almost any LLM pipeline for structured extraction tasks: do as much work as possible with deterministic rules before touching the model.

The AI PDF Renamer applies a scoring pass over the extracted text before deciding whether to call the LLM at all. The heuristics are regex-based rules that look for patterns likely to appear in specific document types:

  • Date patterns: \d{4}-\d{2}-\d{2}, \d{2}\.\d{2}\.\d{4}, and a dozen variants
  • Document type markers: “Rechnung”, “Invoice”, “Beleg”, “Gutschrift”, “Receipt”
  • Author/institution lines near the document header
  • Keywords from a configurable list associated with specific categories

Each rule that fires contributes a score to a candidate metadata record. If the heuristic pass produces a confident result — date found, category identified, a couple of distinguishing keywords present — the LLM call is skipped entirely. The file gets renamed from the heuristic output.

This matters for a few reasons. Heuristics are fast (microseconds vs. seconds for an LLM call), deterministic (the same input always produces the same output), and do not require a running model. For a batch of two hundred invoices from the same vendor, the heuristic pass will handle most of them without any LLM involvement.

The LLM is enrichment for the hard cases: documents with unusual formats, mixed-language content, documents where the type is not obvious from surface features. In practice this is probably 20–40% of a typical mixed-document folder.

Step Four: What to Ask the LLM, and How

When a heuristic pass does not produce a confident result, the pipeline builds a prompt from the extracted text and sends it to the local endpoint. What the prompt asks for matters enormously.

The naive approach: “Please rename this PDF. Here is the content: [text].” The response will be a sentence. Maybe several sentences. It will not be parseable as a filename without further processing, and that further processing is itself an LLM call or a fragile regex.

The better approach: ask for structured output. The prompt in llm_prompts.py requests a JSON object conforming to a schema — something like:

{
  "date": "YYYYMMDD or null",
  "category": "one of: invoice, paper, letter, contract, ...",
  "keywords": ["max 3 short keywords"],
  "summary": "max 5 words"
}

The model returns JSON. The response parser in llm_parsing.py validates it against the schema, catches malformed responses, applies fallbacks for null fields, and sanitises the individual fields before they are assembled into a filename.

This works because JSON is well-represented in LLM training data — models have seen vastly more JSON than they have seen arbitrary prose instructions to parse. A model told to return a specific JSON structure will do so reliably for most inputs. The failure rate (malformed JSON, missing fields, hallucinated values) is low enough to be handled by the fallback logic.

What counts as a hallucinated value in this context? Dates in the future. Categories not in the allowed set. Keywords that are not present in the source text. The llm_schema.py validation layer catches the obvious cases; for subtler errors (a plausible-sounding date that does not appear in the document), the tool relies on the heuristic pass having already identified any date that can be reliably extracted.

Step Five: The Filename

The output format is YYYYMMDD-category-keywords-summary.pdf. A few design decisions embedded in this:

Date first. Lexicographic sorting of filenames then gives you chronological sorting for free. This is the most useful sort order for most document types — you want to find the most recent invoice, not the alphabetically first one.

Lowercase, hyphens only. No spaces (which require escaping in many contexts), no special characters (which are illegal in some filesystems or require quoting), no uppercase (which creates case-sensitivity issues across platforms). The sanitisation step in filename.py strips or replaces anything that does not conform.

Collision resolution. Two documents with the same date, category, keywords, and summary would produce the same filename. The resolver appends a counter suffix (_01, _02, …) when a target name already exists. This is deterministic — the same set of documents always produces the same filenames, regardless of processing order — which matters for the undo log.

Local-First

The LLM endpoint defaults to http://127.0.0.1:11434/v1/completions — Ollama running locally, no external traffic. This is a deliberate choice for a document management tool. The documents being renamed are likely to include medical records, financial statements, legal correspondence — content that should not be routed through an external API by default.

A small 8B model running locally is sufficient for this task. The extraction problem does not require deep reasoning; it requires pattern recognition over a short text and the ability to return a specific JSON structure. Models at this scale handle it well. The latency is measurable (a few seconds per document on a modern laptop with a reasonably fast inference backend) but acceptable for a batch job running in the background.

For users who want to use a remote API, the endpoint is configurable — the local default is a sensible starting point, not a hard constraint.

What It Cannot Do

Renaming is a classification problem disguised as a text generation problem. The tool works well when documents have standard structure — title on page one, date near the header or footer, document type identifiable from a few keywords. It works less well for documents that are structurally atypical: a hand-written letter scanned at poor resolution, a PDF that is essentially a single large image, a document in a language the model handles badly.

The heuristic fallback means that even when the LLM produces a bad result, the file gets a usable if imperfect name rather than a broken one. And the undo log means that a bad batch run can be reversed. These are not complete solutions to the hard cases, but they are the right design response to a tool that handles real-world document noise.

The harder limit is semantic: the tool can tell you that a document is an invoice and extract its date and vendor name. It cannot tell you whether the invoice has been paid, whether it matches a purchase order, or whether the amount is correct. For those questions, renaming is just the first step in a longer pipeline.

The repository is at github.com/sebastianspicker/AI-PDF-Renamer. The tokenisation background in the extraction and budgeting sections connects to the strawberry tokenisation post and the context window post.

Changelog

  • 2026-04-02: Corrected the default model name from qwen3:8b to qwen2.5:3b. The codebase default is qwen2.5:3b (apple-silicon preset) or qwen2.5:7b-instruct (gpu preset).
  • 2026-04-02: Corrected DEFAULT_MAX_CONTENT_TOKENS description from “28,000 characters … roughly 7,000 tokens” to “28,000 tokens.” The variable is a token limit, not a character limit.