diff --git a/client/components/modals/libraries/EditModal.vue b/client/components/modals/libraries/EditModal.vue
index a6d8a4d5..930eaf29 100644
--- a/client/components/modals/libraries/EditModal.vue
+++ b/client/components/modals/libraries/EditModal.vue
@@ -127,6 +127,7 @@ export default {
           autoScanCronExpression: null,
           hideSingleBookSeries: false,
           onlyShowLaterBooksInContinueSeries: false,
+          openAIDirectoryGrouping: false,
           metadataPrecedence: ['folderStructure', 'audioMetatags', 'nfoFile', 'txtFiles', 'opfFile', 'absMetadata'],
           markAsFinishedPercentComplete: null,
           markAsFinishedTimeRemaining: 10
diff --git a/client/components/modals/libraries/LibraryScannerSettings.vue b/client/components/modals/libraries/LibraryScannerSettings.vue
index 686e77e4..29548c62 100644
--- a/client/components/modals/libraries/LibraryScannerSettings.vue
+++ b/client/components/modals/libraries/LibraryScannerSettings.vue
@@ -1,5 +1,12 @@
 <template>
   <div class="w-full h-full px-1 md:px-4 py-1 mb-4">
+    <div class="flex items-center justify-between md:justify-start mb-4">
+      <div class="flex items-center">
+        <ui-toggle-switch v-model="openAIDirectoryGrouping" @input="updated" />
+        <p class="pl-4 text-sm text-gray-300">Use OpenAI to interpret poor directory trees during library scans</p>
+      </div>
+    </div>
+
     <div class="flex items-center justify-between mb-2">
       <h2 class="text-base md:text-lg text-gray-200">{{ $strings.HeaderMetadataOrderOfPrecedence }}</h2>
       <ui-btn small @click="resetToDefault">{{ $strings.ButtonResetToDefault }}</ui-btn>
@@ -92,7 +99,8 @@ export default {
           include: true
         }
       },
-      metadataSourceMapped: []
+      metadataSourceMapped: [],
+      openAIDirectoryGrouping: false
     }
   },
   computed: {
@@ -131,6 +139,7 @@ export default {
       metadataSourceIds.reverse()
       return {
         settings: {
+          openAIDirectoryGrouping: !!this.openAIDirectoryGrouping,
           metadataPrecedence: metadataSourceIds
         }
       }
@@ -145,6 +154,7 @@ export default {
       this.$emit('update', this.getLibraryData())
     },
     init() {
+      this.openAIDirectoryGrouping = !!this.librarySettings.openAIDirectoryGrouping
       const metadataPrecedence = this.librarySettings.metadataPrecedence || []
       this.metadataSourceMapped = metadataPrecedence.map((source) => this.metadataSourceData[source]).filter((s) => s)
 
diff --git a/server/models/Library.js b/server/models/Library.js
index 708880aa..483b8d71 100644
--- a/server/models/Library.js
+++ b/server/models/Library.js
@@ -11,6 +11,7 @@ const Logger = require('../Logger')
  * @property {boolean} audiobooksOnly
  * @property {boolean} hideSingleBookSeries Do not show series that only have 1 book
  * @property {boolean} onlyShowLaterBooksInContinueSeries Skip showing books that are earlier than the max sequence read
+ * @property {boolean} openAIDirectoryGrouping Allow OpenAI to infer library-item grouping from poor directory structures
  * @property {string[]} metadataPrecedence
  * @property {number} markAsFinishedTimeRemaining Time remaining in seconds to mark as finished. (defaults to 10s)
  * @property {number} markAsFinishedPercentComplete Percent complete to mark as finished (0-100). If this is set it will be used over markAsFinishedTimeRemaining.
@@ -74,6 +75,7 @@ class Library extends Model {
         epubsAllowScriptedContent: false,
         hideSingleBookSeries: false,
         onlyShowLaterBooksInContinueSeries: false,
+        openAIDirectoryGrouping: false,
         metadataPrecedence: this.defaultMetadataPrecedence,
         markAsFinishedPercentComplete: null,
         markAsFinishedTimeRemaining: 10
diff --git a/server/providers/OpenAI.js b/server/providers/OpenAI.js
index 9e75b740..6d08cd99 100644
--- a/server/providers/OpenAI.js
+++ b/server/providers/OpenAI.js
@@ -42,6 +42,14 @@ class OpenAI {
     })
   }
 
+  summarizeDirectoryGroupingForLog(grouping) {
+    return JSON.stringify({
+      path: grouping.path,
+      groupId: grouping.groupId,
+      reason: grouping.reason || ''
+    })
+  }
+
   normalizePathForPrompt(filePath) {
     if (!filePath || typeof filePath !== 'string') return null
     return filePath.replace(/\\/g, '/')
@@ -272,6 +280,42 @@ class OpenAI {
     }
   }
 
+  validateDirectoryGroupingPayload(payload, mediaFiles) {
+    const resultFiles = payload?.files
+    if (!Array.isArray(resultFiles)) {
+      throw new Error('OpenAI returned invalid directory-grouping payload')
+    }
+
+    const expectedPaths = new Set(mediaFiles.map((file) => file.path))
+    const resultByPath = new Map()
+
+    resultFiles.forEach((file) => {
+      if (!expectedPaths.has(file?.path)) {
+        Logger.warn(`[OpenAI] Ignoring unknown media path "${file?.path}" in directory-grouping response`)
+        return
+      }
+      if (resultByPath.has(file.path)) {
+        Logger.warn(`[OpenAI] Ignoring duplicate media path "${file.path}" in directory-grouping response`)
+        return
+      }
+      resultByPath.set(file.path, file)
+    })
+
+    return mediaFiles.map((file) => {
+      const result = resultByPath.get(file.path)
+      const groupId = this.normalizeOptionalString(result?.groupId, 120) || file.path
+      const reason = this.normalizeOptionalString(result?.reason, 600) || (result ? '' : 'OpenAI omitted this media file; kept it as its own item')
+      if (!result) {
+        Logger.warn(`[OpenAI] Missing directory-grouping result for media path "${file.path}" - keeping it separate`)
+      }
+      return {
+        path: file.path,
+        groupId,
+        reason
+      }
+    })
+  }
+
   validateBookIds(resultBooks, books) {
     if (!Array.isArray(resultBooks) || resultBooks.length !== books.length) {
       throw new Error('OpenAI returned an invalid number of books')
@@ -649,6 +693,55 @@ ${JSON.stringify(ebookMetadata, null, 2)}`
     Logger.info(`[OpenAI] Scan-metadata result for "${libraryItemData.relPath}" ${this.summarizeScanMetadataForLog(validated)}`)
     return validated
   }
+
+  async inferDirectoryGroupingFromPaths(containerPath, mediaFiles) {
+    if (!this.isConfigured) {
+      throw new Error('OpenAI API key is not configured')
+    }
+    if (!Array.isArray(mediaFiles) || !mediaFiles.length) {
+      return []
+    }
+
+    Logger.info(`[OpenAI] Inferring directory grouping for "${containerPath}" with ${mediaFiles.length} media files`)
+    mediaFiles.forEach((file) => {
+      Logger.info(`[OpenAI] Directory-grouping candidate ${JSON.stringify(file)}`)
+    })
+
+    const prompt = `You infer logical audiobook item grouping from messy filesystem paths.
+
+Return only valid JSON in this shape:
+{
+  "files": [
+    {
+      "path": "relative/path/to/media-file.m4b",
+      "groupId": "short-group-label",
+      "reason": "brief reason"
+    }
+  ]
+}
+
+Rules:
+- Include every provided media file exactly once.
+- Files that belong to the same logical audiobook item must share the same groupId.
+- Files for different books must use different groupIds even if they are in the same series container.
+- Use path, filename, parent directories, and current grouping hints as evidence.
+- Prefer preserving existing grouping when it already looks reasonable.
+- Do not merge different titled books just because they share a series or author folder.
+- groupId only needs to be stable within this one response.
+
+Container path:
+${JSON.stringify(containerPath)}
+
+Media files:
+${JSON.stringify(mediaFiles, null, 2)}`
+
+    const payload = await this.createResponse(prompt)
+    const validated = this.validateDirectoryGroupingPayload(payload, mediaFiles)
+    validated.forEach((grouping) => {
+      Logger.info(`[OpenAI] Directory-grouping result ${this.summarizeDirectoryGroupingForLog(grouping)}`)
+    })
+    return validated
+  }
 }
 
 module.exports = OpenAI
diff --git a/server/scanner/LibraryScanner.js b/server/scanner/LibraryScanner.js
index 63670322..1c55fc45 100644
--- a/server/scanner/LibraryScanner.js
+++ b/server/scanner/LibraryScanner.js
@@ -7,6 +7,7 @@ const Database = require('../Database')
 const fs = require('../libs/fsExtra')
 const fileUtils = require('../utils/fileUtils')
 const scanUtils = require('../utils/scandir')
+const globals = require('../utils/globals')
 const { LogLevel, ScanResult } = require('../utils/constants')
 const libraryFilters = require('../utils/queries/libraryFilters')
 const TaskManager = require('../managers/TaskManager')
@@ -14,6 +15,10 @@ const LibraryItemScanner = require('./LibraryItemScanner')
 const LibraryScan = require('./LibraryScan')
 const LibraryItemScanData = require('./LibraryItemScanData')
 const Task = require('../objects/Task')
+const OpenAI = require('../providers/OpenAI')
+
+const openAI = new OpenAI()
+const DISC_DIR_REGEX = /^(cd|dis[ck])\s*\d{1,3}$/i
 
 class LibraryScanner {
   constructor() {
@@ -309,7 +314,10 @@ class LibraryScanner {
     }
 
     const fileItems = await fileUtils.recurseFiles(folderPath)
-    const libraryItemGrouping = scanUtils.groupFileItemsIntoLibraryItemDirs(library.mediaType, fileItems, library.settings.audiobooksOnly)
+    let libraryItemGrouping = scanUtils.groupFileItemsIntoLibraryItemDirs(library.mediaType, fileItems, library.settings.audiobooksOnly)
+    if (library.mediaType === 'book' && library.settings.openAIDirectoryGrouping && openAI.isConfigured) {
+      libraryItemGrouping = await this.applyOpenAIDirectoryGrouping(folderPath, fileItems, libraryItemGrouping, library.settings.audiobooksOnly)
+    }
 
     if (!Object.keys(libraryItemGrouping).length) {
       Logger.error(`Root path has no media folders: ${folderPath}`)
@@ -368,6 +376,201 @@ class LibraryScanner {
     return items
   }
 
+  expandGroupingFiles(groupPath, groupedFiles) {
+    if (groupPath === groupedFiles) return [groupPath]
+    return groupedFiles.map((file) => {
+      if (file === groupPath || file.startsWith(groupPath + '/')) return file
+      return Path.posix.join(groupPath, file)
+    })
+  }
+
+  getOpenAIDirectoryGroupingCandidates(fileItems, mediaType, audiobooksOnly, libraryItemGrouping) {
+    if (mediaType !== 'book') return []
+
+    const mediaFileItems = fileItems.filter((item) => isMediaFilePath(mediaType, item.path, audiobooksOnly))
+    const candidatesByContainer = new Map()
+
+    mediaFileItems.forEach((item) => {
+      const topLevelDir = item.path.split('/').filter(Boolean)[0]
+      if (!topLevelDir || !item.path.includes('/')) return
+      if (!candidatesByContainer.has(topLevelDir)) {
+        candidatesByContainer.set(topLevelDir, [])
+      }
+      candidatesByContainer.get(topLevelDir).push(item)
+    })
+
+    return [...candidatesByContainer.entries()]
+      .map(([containerPath, containerMediaFileItems]) => {
+        const defaultGroupKeys = Object.keys(libraryItemGrouping).filter((groupPath) => groupPath === containerPath || groupPath.startsWith(containerPath + '/'))
+        const hasDirectMediaFileInContainer = containerMediaFileItems.some((item) => Path.posix.dirname(item.path) === containerPath)
+        const hasMixedDefaultFileAndDirectoryGroups =
+          defaultGroupKeys.some((groupPath) => Path.posix.extname(groupPath)) && defaultGroupKeys.some((groupPath) => !Path.posix.extname(groupPath))
+        const maxRelativeDepth = Math.max(...containerMediaFileItems.map((item) => Path.posix.relative(containerPath, item.path).split('/').filter(Boolean).length))
+        const suspicious = defaultGroupKeys.length <= 1 || hasDirectMediaFileInContainer || hasMixedDefaultFileAndDirectoryGroups || maxRelativeDepth > 2
+
+        if (!suspicious || containerMediaFileItems.length < 2 || containerMediaFileItems.length > 40) {
+          return null
+        }
+
+        const groupingHints = containerMediaFileItems.map((item) => ({
+          path: item.path,
+          filename: item.name,
+          parentDir: item.reldirpath || '',
+          folderHierarchy: item.path.split('/').slice(0, -1).filter(Boolean),
+          currentGroup: defaultGroupKeys.find((groupPath) => this.expandGroupingFiles(groupPath, libraryItemGrouping[groupPath]).includes(item.path)) || null
+        }))
+
+        return {
+          containerPath,
+          groupingHints
+        }
+      })
+      .filter(Boolean)
+  }
+
+  getDirectoryGroupingDescriptor(containerPath, mediaPaths) {
+    const sortedMediaPaths = [...mediaPaths].sort((a, b) => a.localeCompare(b))
+    if (sortedMediaPaths.length === 1) {
+      const mediaDir = Path.posix.dirname(sortedMediaPaths[0])
+      if (mediaDir && mediaDir !== '.' && mediaDir !== containerPath) {
+        return {
+          groupPath: mediaDir,
+          isFile: false
+        }
+      }
+      return {
+        groupPath: sortedMediaPaths[0],
+        isFile: true
+      }
+    }
+
+    const splitPaths = sortedMediaPaths.map((mediaPath) => mediaPath.split('/'))
+    const commonParts = []
+    for (let i = 0; i < Math.min(...splitPaths.map((parts) => parts.length - 1)); i++) {
+      const segment = splitPaths[0][i]
+      if (splitPaths.every((parts) => parts[i] === segment)) {
+        commonParts.push(segment)
+      } else {
+        break
+      }
+    }
+    const commonDir = commonParts.join('/')
+
+    if (commonDir) {
+      const canUseFolderGroup = sortedMediaPaths.every((mediaPath) => {
+        const relativeParts = Path.posix.relative(commonDir, mediaPath).split('/').filter(Boolean)
+        return relativeParts.length === 1 || (relativeParts.length === 2 && DISC_DIR_REGEX.test(relativeParts[0]))
+      })
+
+      if (canUseFolderGroup) {
+        return {
+          groupPath: commonDir,
+          isFile: false
+        }
+      }
+    }
+
+    return {
+      groupPath: sortedMediaPaths[0],
+      isFile: true
+    }
+  }
+
+  buildLibraryItemGroupingFromOpenAIAssignments(containerPath, fileItems, assignments, mediaType, audiobooksOnly) {
+    const mediaPathsByGroupId = new Map()
+    assignments.forEach((assignment) => {
+      if (!mediaPathsByGroupId.has(assignment.groupId)) {
+        mediaPathsByGroupId.set(assignment.groupId, [])
+      }
+      mediaPathsByGroupId.get(assignment.groupId).push(assignment.path)
+    })
+
+    const groupRecords = [...mediaPathsByGroupId.entries()].map(([groupId, mediaPaths]) => {
+      const descriptor = this.getDirectoryGroupingDescriptor(containerPath, mediaPaths)
+      return {
+        groupId,
+        descriptor,
+        mediaPaths: [...mediaPaths].sort((a, b) => a.localeCompare(b)),
+        files: []
+      }
+    })
+
+    groupRecords.forEach((groupRecord) => {
+      if (groupRecord.descriptor.isFile) {
+        groupRecord.files.push(...groupRecord.mediaPaths)
+      } else {
+        groupRecord.files.push(...groupRecord.mediaPaths.map((mediaPath) => Path.posix.relative(groupRecord.descriptor.groupPath, mediaPath)))
+      }
+    })
+
+    const nonMediaItems = fileItems.filter((item) => !isMediaFilePath(mediaType, item.path, audiobooksOnly))
+    nonMediaItems.forEach((item) => {
+      const itemStem = Path.basename(item.name, item.extension)
+
+      let matchingGroup = null
+      const basenameMatches = groupRecords.filter((groupRecord) =>
+        groupRecord.mediaPaths.some((mediaPath) => Path.posix.dirname(mediaPath) === item.reldirpath && Path.basename(mediaPath, Path.extname(mediaPath)) === itemStem)
+      )
+      if (basenameMatches.length === 1) {
+        matchingGroup = basenameMatches[0]
+      }
+
+      if (!matchingGroup) {
+        const directoryMatches = groupRecords.filter((groupRecord) => {
+          if (!groupRecord.descriptor.isFile) {
+            return item.path.startsWith(groupRecord.descriptor.groupPath + '/')
+          }
+          return Path.posix.dirname(groupRecord.descriptor.groupPath) === item.reldirpath
+        })
+        if (directoryMatches.length === 1) {
+          matchingGroup = directoryMatches[0]
+        }
+      }
+
+      if (!matchingGroup) return
+
+      const fileEntry = matchingGroup.descriptor.isFile ? item.path : Path.posix.relative(matchingGroup.descriptor.groupPath, item.path)
+      if (!matchingGroup.files.includes(fileEntry)) {
+        matchingGroup.files.push(fileEntry)
+      }
+    })
+
+    return groupRecords.reduce((acc, groupRecord) => {
+      acc[groupRecord.descriptor.groupPath] = [...new Set(groupRecord.files)]
+      return acc
+    }, {})
+  }
+
+  async applyOpenAIDirectoryGrouping(folderPath, fileItems, libraryItemGrouping, audiobooksOnly) {
+    const candidates = this.getOpenAIDirectoryGroupingCandidates(fileItems, 'book', audiobooksOnly, libraryItemGrouping)
+    if (!candidates.length) return libraryItemGrouping
+
+    let updatedGrouping = { ...libraryItemGrouping }
+    for (const candidate of candidates) {
+      Logger.info(`[LibraryScanner] Evaluating OpenAI directory grouping for "${candidate.containerPath}" with ${candidate.groupingHints.length} media files`)
+      const containerFileItems = fileItems.filter((item) => item.path === candidate.containerPath || item.path.startsWith(candidate.containerPath + '/'))
+      const assignments = await openAI.inferDirectoryGroupingFromPaths(candidate.containerPath, candidate.groupingHints).catch((error) => {
+        Logger.warn(`[LibraryScanner] OpenAI directory grouping failed for "${candidate.containerPath}": ${error.message}`)
+        return null
+      })
+      if (!assignments?.length) continue
+
+      const aiGrouping = this.buildLibraryItemGroupingFromOpenAIAssignments(candidate.containerPath, containerFileItems, assignments, 'book', audiobooksOnly)
+      if (!Object.keys(aiGrouping).length) continue
+
+      updatedGrouping = Object.fromEntries(
+        Object.entries(updatedGrouping).filter(([groupPath]) => !(groupPath === candidate.containerPath || groupPath.startsWith(candidate.containerPath + '/')))
+      )
+      updatedGrouping = {
+        ...updatedGrouping,
+        ...aiGrouping
+      }
+      Logger.info(`[LibraryScanner] Applied OpenAI directory grouping for "${candidate.containerPath}" -> ${Object.keys(aiGrouping).length} library items`)
+    }
+
+    return updatedGrouping
+  }
+
   /**
    * Scan files changed from Watcher
    * @param {import('../Watcher').PendingFileUpdate[]} fileUpdates
@@ -650,6 +853,14 @@ function ItemToFileInoMatch(libraryItem1, libraryItem2) {
   return libraryItem1.isFile && libraryItem2.libraryFiles.some((lf) => lf.ino === libraryItem1.ino)
 }
 
+function isMediaFilePath(mediaType, filepath, audiobooksOnly = false) {
+  const ext = Path.extname(filepath).slice(1).toLowerCase()
+  if (!ext) return false
+  if (mediaType === 'podcast') return globals.SupportedAudioTypes.includes(ext)
+  if (audiobooksOnly) return globals.SupportedAudioTypes.includes(ext)
+  return globals.SupportedAudioTypes.includes(ext) || globals.SupportedEbookTypes.includes(ext)
+}
+
 function ItemToItemInoMatch(libraryItem1, libraryItem2) {
   return libraryItem1.ino === libraryItem2.ino
 }
diff --git a/test/server/providers/OpenAI.test.js b/test/server/providers/OpenAI.test.js
index c55e5926..53fed180 100644
--- a/test/server/providers/OpenAI.test.js
+++ b/test/server/providers/OpenAI.test.js
@@ -179,4 +179,37 @@ describe('OpenAI', () => {
       expect(result.isbn).to.equal(null)
     })
   })
+
+  describe('validateDirectoryGroupingPayload', () => {
+    it('normalizes valid directory-grouping payload', () => {
+      const result = openAI.validateDirectoryGroupingPayload(
+        {
+          files: [
+            { path: 'Series Alpha/Book One.m4b', groupId: ' book-one ', reason: 'same book' },
+            { path: 'Series Alpha/Disc 1/Book Two Part 1.mp3', groupId: 'book-two', reason: 'disc set' }
+          ]
+        },
+        [{ path: 'Series Alpha/Book One.m4b' }, { path: 'Series Alpha/Disc 1/Book Two Part 1.mp3' }]
+      )
+
+      expect(result[0].groupId).to.equal('book-one')
+      expect(result[1].groupId).to.equal('book-two')
+    })
+
+    it('backfills missing or invalid grouping rows', () => {
+      const result = openAI.validateDirectoryGroupingPayload(
+        {
+          files: [
+            { path: 'unknown/path.m4b', groupId: 'ignored' },
+            { path: 'Series Alpha/Book One.m4b', groupId: '' }
+          ]
+        },
+        [{ path: 'Series Alpha/Book One.m4b' }, { path: 'Series Alpha/Book Two.m4b' }]
+      )
+
+      expect(result[0].groupId).to.equal('Series Alpha/Book One.m4b')
+      expect(result[1].groupId).to.equal('Series Alpha/Book Two.m4b')
+      expect(result[1].reason).to.contain('omitted this media file')
+    })
+  })
 })