diff --git a/server/Database.js b/server/Database.js
index 213c2c61b..7a0f342d5 100644
--- a/server/Database.js
+++ b/server/Database.js
@@ -966,6 +966,20 @@ WHERE EXISTS (
       return `unaccent(${value})`
     }
 
+    /**
+     * Returns an expression that strips punctuation the older in-memory search ignored.
+     *
+     * @param {string} expression
+     * @returns {string}
+     */
+    stripPunctuation(expression) {
+      const punctuationChars = ["'", '.', '`', '"', ',']
+      punctuationChars.forEach((char) => {
+        expression = `replace(${expression}, ${this.sequelize.escape(char)}, '')`
+      })
+      return expression
+    }
+
     /**
      * Initialize the text query.
      *
@@ -983,15 +997,17 @@ WHERE EXISTS (
      * Get match expression for the specified column.
      * If the query contains accents, match against the column as-is (case-insensitive exact match).
      * otherwise match against a normalized column (case-insensitive match with accents removed).
+     * Punctuation is stripped from both sides in all cases.
      *
      * @param {string} column
      * @returns {string}
      */
     matchExpression(column) {
-      const pattern = this.sequelize.escape(`%${this.query}%`)
-      if (!this.supportsUnaccent) return `${column} LIKE ${pattern}`
+      const queryExpr = this.stripPunctuation(this.sequelize.escape(this.query))
+      const pattern = `'%' || ${queryExpr} || '%'`
+      if (!this.supportsUnaccent) return `${this.stripPunctuation(column)} LIKE ${pattern}`
       const normalizedColumn = this.hasAccents ? column : this.normalize(column)
-      return `${normalizedColumn} LIKE ${pattern}`
+      return `${this.stripPunctuation(normalizedColumn)} LIKE ${pattern}`
     }
   }
 }
diff --git a/test/server/utils/queries/libraryItemsBookFilters.test.js b/test/server/utils/queries/libraryItemsBookFilters.test.js
new file mode 100644
index 000000000..8fe8181f1
--- /dev/null
+++ b/test/server/utils/queries/libraryItemsBookFilters.test.js
@@ -0,0 +1,69 @@
+const { expect } = require('chai')
+const { Sequelize } = require('sequelize')
+
+const Database = require('../../../../server/Database')
+const libraryItemsBookFilters = require('../../../../server/utils/queries/libraryItemsBookFilters')
+
+describe('libraryItemsBookFilters.search', () => {
+  beforeEach(async () => {
+    global.ServerSettings = {}
+    Database.sequelize = new Sequelize({ dialect: 'sqlite', storage: ':memory:', logging: false })
+    Database.sequelize.uppercaseFirst = (str) => (str ? `${str[0].toUpperCase()}${str.substr(1)}` : '')
+    Database.supportsUnaccent = false
+    await Database.buildModels()
+  })
+
+  afterEach(async () => {
+    await Database.sequelize.sync({ force: true })
+  })
+
+  it('matches titles when the query omits commas', async () => {
+    const library = await Database.libraryModel.create({ name: 'Test Library', mediaType: 'book' })
+    const libraryFolder = await Database.libraryFolderModel.create({ path: '/test', libraryId: library.id })
+    const book = await Database.bookModel.create({
+      title: 'And Now, Back to You',
+      audioFiles: [],
+      tags: [],
+      narrators: [],
+      genres: [],
+      chapters: []
+    })
+    await Database.libraryItemModel.create({
+      libraryFiles: [],
+      mediaId: book.id,
+      mediaType: 'book',
+      libraryId: library.id,
+      libraryFolderId: libraryFolder.id
+    })
+
+    const results = await libraryItemsBookFilters.search(null, library, 'And Now Back to You', 10, 0)
+
+    expect(results.book).to.have.length(1)
+    expect(results.book[0].libraryItem.media.metadata.title).to.equal('And Now, Back to You')
+  })
+
+  it('matches titles when the query omits apostrophes', async () => {
+    const library = await Database.libraryModel.create({ name: 'Test Library', mediaType: 'book' })
+    const libraryFolder = await Database.libraryFolderModel.create({ path: '/test', libraryId: library.id })
+    const book = await Database.bookModel.create({
+      title: "Don't Panic",
+      audioFiles: [],
+      tags: [],
+      narrators: [],
+      genres: [],
+      chapters: []
+    })
+    await Database.libraryItemModel.create({
+      libraryFiles: [],
+      mediaId: book.id,
+      mediaType: 'book',
+      libraryId: library.id,
+      libraryFolderId: libraryFolder.id
+    })
+
+    const results = await libraryItemsBookFilters.search(null, library, 'Dont Panic', 10, 0)
+
+    expect(results.book).to.have.length(1)
+    expect(results.book[0].libraryItem.media.metadata.title).to.equal("Don't Panic")
+  })
+})