diff --git a/lib/add_book.go b/lib/add_book.go
index 4b8ae4c..e0aa343 100644
--- a/lib/add_book.go
+++ b/lib/add_book.go
@@ -1,6 +1,8 @@
 package lib
 
 import (
+	"fmt"
+
 	"github.com/samber/lo"
 )
 
@@ -54,44 +56,44 @@ func AddBook(url string, options addBookOptions) (Book, error) {
 		}
 
 		if err := validateURL(NullStringFrom(url)); err != nil {
-			return book, err
+			return book, fmt.Errorf("URL validation failed while adding bookmark: %w", err)
 		}
 
 		if err := validateName(options.name); err != nil {
-			return book, err
+			return book, fmt.Errorf("name validation failed while adding bookmark: %w", err)
 		}
 
 		if err := validateDescription(options.description); err != nil {
-			return book, err
+			return book, fmt.Errorf("description validation failed while adding bookmark: %w", err)
 		}
 
 		if err := validateParentID(tx, options.parentID); err != nil {
-			return book, err
+			return book, fmt.Errorf("parent ID validation failed while adding bookmark: %w", err)
 		}
 
 		if err := validateTags(options.tags, make([]string, 0)); err != nil {
-			return book, err
+			return book, fmt.Errorf("tags validation failed while adding bookmark: %w", err)
 		}
 
 		id, err := addBookDB(tx, url, options.name.String, options.description, options.parentID)
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error while adding bookmark: %w", err)
 		}
 
 		existingTags, err := getTagsDB(tx, getTagsDBArgs{
 			tagsFilter: options.tags,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error getting tags while adding bookmark: %w", err)
 		}
 
 		tagsToAdd, _ := lo.Difference(options.tags, existingTags)
 		if err = addTagsDB(tx, tagsToAdd); err != nil {
-			return book, err
+			return book, fmt.Errorf("error adding tags while adding bookmark: %w", err)
 		}
 
 		if err = linkTagsDB(tx, id, options.tags); err != nil {
-			return book, err
+			return book, fmt.Errorf("error linking tags while adding bookmark: %w", err)
 		}
 
 		books, err := getBooksDB(tx, getBooksDBArgs{
@@ -99,9 +101,9 @@ func AddBook(url string, options addBookOptions) (Book, error) {
 			includeBooks: true,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error getting bookmarks while adding bookmark: %w", err)
 		}
 
-		return books[0], err
+		return books[0], nil
 	})
 }
diff --git a/lib/add_folder.go b/lib/add_folder.go
index 7dbfc03..70199fe 100644
--- a/lib/add_folder.go
+++ b/lib/add_folder.go
@@ -1,5 +1,9 @@
 package lib
 
+import (
+	"fmt"
+)
+
 // addFolderOptions are the optional arguments for AddFolder.
 type addFolderOptions struct {
 	db       NullString
@@ -27,16 +31,16 @@ func AddFolder(name string, options addFolderOptions) (Book, error) {
 		var book Book
 
 		if err := validateName(NullStringFrom(name)); err != nil {
-			return book, err
+			return book, fmt.Errorf("name validation failed while adding folder: %w", err)
 		}
 
 		if err := validateParentID(tx, options.parentID); err != nil {
-			return book, err
+			return book, fmt.Errorf("parent ID validation failed while adding folder: %w", err)
 		}
 
 		id, err := addFolderDB(tx, name, options.parentID)
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error while adding folder: %w", err)
 		}
 
 		books, err := getBooksDB(tx, getBooksDBArgs{
@@ -44,9 +48,9 @@ func AddFolder(name string, options addFolderOptions) (Book, error) {
 			includeFolders: true,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error getting folders while adding folder: %w", err)
 		}
 
-		return books[0], err
+		return books[0], nil
 	})
 }
diff --git a/lib/add_tags.go b/lib/add_tags.go
index 7e3c203..a483213 100644
--- a/lib/add_tags.go
+++ b/lib/add_tags.go
@@ -1,6 +1,8 @@
 package lib
 
 import (
+	"fmt"
+
 	"github.com/samber/lo"
 )
 
@@ -29,7 +31,7 @@ func AddTags(id string, tags []string, options addTagsOptions) (Book, error) {
 			includeBooks: true,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error getting tags while adding tags: %w", err)
 		}
 
 		if len(books) != 1 || books[0].IsFolder {
@@ -37,7 +39,7 @@ func AddTags(id string, tags []string, options addTagsOptions) (Book, error) {
 		}
 
 		if err := validateTags(tags, books[0].Tags); err != nil {
-			return book, err
+			return book, fmt.Errorf("tags validation failed while adding tags: %w", err)
 		}
 
 		existingTags, err := getTagsDB(tx, getTagsDBArgs{
@@ -49,11 +51,11 @@ func AddTags(id string, tags []string, options addTagsOptions) (Book, error) {
 
 		tagsToAdd, _ := lo.Difference(tags, existingTags)
 		if err = addTagsDB(tx, tagsToAdd); err != nil {
-			return book, err
+			return book, fmt.Errorf("error while adding tags: %w", err)
 		}
 
 		if err = linkTagsDB(tx, id, tags); err != nil {
-			return book, err
+			return book, fmt.Errorf("error linking tags while adding tags: %w", err)
 		}
 
 		books, err = getBooksDB(tx, getBooksDBArgs{
@@ -61,7 +63,7 @@ func AddTags(id string, tags []string, options addTagsOptions) (Book, error) {
 			includeBooks: true,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error getting bookmarks while adding tags: %w", err)
 		}
 
 		return books[0], nil
diff --git a/lib/config.go b/lib/config.go
index 8995ece..c8fb93b 100644
--- a/lib/config.go
+++ b/lib/config.go
@@ -2,6 +2,7 @@ package lib
 
 import (
 	"errors"
+	"fmt"
 	"os"
 	"path/filepath"
 	"runtime"
@@ -40,7 +41,7 @@ func GetConfig() (Config, error) {
 
 	configPath, err := getConfigPath(runtime.GOOS, os.UserHomeDir, filepath.Join)
 	if err != nil {
-		return config, err
+		return config, fmt.Errorf("error getting config path while getting config: %w", err)
 	}
 
 	var k = koanf.New(".")
@@ -48,13 +49,13 @@ func GetConfig() (Config, error) {
 		if strings.Contains(err.Error(), "no such file or directory") {
 			return config, ErrConfigMissing
 		} else {
-			return config, err
+			return config, fmt.Errorf("error loading config while getting config: %w", err)
 		}
 	}
 
 	err = k.Unmarshal("", &config)
 	if err != nil {
-		return config, err
+		return config, fmt.Errorf("error unmarshalling config while getting config: %w", err)
 	}
 
 	return config, nil
@@ -65,18 +66,18 @@ func GetConfig() (Config, error) {
 func UpdateConfig(update updateConfigFn) error {
 	config, err := GetConfig()
 	if err != nil && !errors.Is(err, ErrConfigMissing) {
-		return err
+		return fmt.Errorf("error getting config while updating config: %w", err)
 	}
 
 	if errors.Is(err, ErrConfigMissing) {
 		folder, err := getFolderPath(runtime.GOOS, os.UserHomeDir, filepath.Join)
 		if err != nil {
-			return err
+			return fmt.Errorf("error getting config folder path while updating config: %w", err)
 		}
 
 		err = os.MkdirAll(folder, os.ModePerm)
 		if err != nil {
-			return err
+			return fmt.Errorf("error making config folder while updating config: %w", err)
 		}
 	}
 
@@ -85,28 +86,28 @@ func UpdateConfig(update updateConfigFn) error {
 	var k = koanf.New(".")
 	err = k.Load(structs.Provider(config, "koanf"), nil)
 	if err != nil {
-		return err
+		return fmt.Errorf("error loading config while updating config: %w", err)
 	}
 
 	buffer, err := k.Marshal(toml.Parser())
 	if err != nil {
-		return err
+		return fmt.Errorf("error marshalling config while updating config: %w", err)
 	}
 
 	configPath, err := getConfigPath(runtime.GOOS, os.UserHomeDir, filepath.Join)
 	if err != nil {
-		return err
+		return fmt.Errorf("error getting config path while updating config: %w", err)
 	}
 
 	handle, err := os.Create(configPath)
 	if err != nil {
-		return err
+		return fmt.Errorf("error creating config file while updating config: %w", err)
 	}
 	defer handle.Close()
 
 	_, err = handle.Write(buffer)
 	if err != nil {
-		return err
+		return fmt.Errorf("error writing config file contents while updating config: %w", err)
 	}
 
 	return nil
@@ -125,11 +126,11 @@ func getDatabasePath(inputPath NullString, configPath string, goos string, mkDir
 	} else {
 		folder, err := getFolderPath(goos, userHome, join)
 		if err != nil {
-			return "", err
+			return "", fmt.Errorf("error getting folder path while getting database path: %w", err)
 		}
 
 		if err = mkDirAll(folder, os.ModePerm); err != nil {
-			return "", err
+			return "", fmt.Errorf("error creating folder while getting database path: %w", err)
 		}
 
 		return join(folder, databaseFilename), nil
@@ -141,7 +142,7 @@ func getDatabasePath(inputPath NullString, configPath string, goos string, mkDir
 func getConfigPath(goos string, userHome userHomeFn, join joinFn) (string, error) {
 	folder, err := getFolderPath(goos, userHome, join)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("error getting folder path while getting config path: %w", err)
 	}
 
 	return join(folder, configFilename), nil
@@ -155,7 +156,7 @@ func getConfigPath(goos string, userHome userHomeFn, join joinFn) (string, error
 func getFolderPath(goos string, userHome userHomeFn, join joinFn) (string, error) {
 	home, err := userHome()
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("error getting home path while getting folder path: %w", err)
 	}
 
 	var folder string
diff --git a/lib/errors.go b/lib/errors.go
index 5824e99..46ab93f 100644
--- a/lib/errors.go
+++ b/lib/errors.go
@@ -5,8 +5,6 @@ import (
 )
 
 var (
-	// ErrUnexpected is returned when an unexpected error occurs.
-	ErrUnexpected = errors.New("unexpected error")
 	// ErrNoUpdate is returned when an update is requested with no updates.
 	ErrNoUpdate = errors.New("no update")
 	// ErrBookNotFound is returned when a target bookmark was not found.
@@ -46,5 +44,5 @@ var (
 	// ErrQueryTooShort is returned when a provided query is too short.
 	ErrQueryTooShort = errors.New("query too short")
 	// ErrConfigMissing is returned when the config file is missing.
-	ErrConfigMissing = errors.New("config is missing")
+	ErrConfigMissing = errors.New("config missing")
 )
diff --git a/lib/list_books.go b/lib/list_books.go
index dbccc9d..02e74d8 100644
--- a/lib/list_books.go
+++ b/lib/list_books.go
@@ -1,5 +1,9 @@
 package lib
 
+import (
+	"fmt"
+)
+
 // listBooksOptions are the optional arguments for ListBooks.
 type listBooksOptions struct {
 	db               NullString
@@ -89,22 +93,22 @@ func ListBooks(options listBooksOptions) ([]Book, error) {
 		}
 
 		if err := validateFirst(options.first); err != nil {
-			return books, err
+			return books, fmt.Errorf("first validation failed while listing bookmarks: %w", err)
 		}
 
 		if err := validateDirection(options.direction); err != nil {
-			return books, err
+			return books, fmt.Errorf("direction validation failed while listing bookmarks: %w", err)
 		}
 
 		if err := validateOrder(options.order); err != nil {
-			return books, err
+			return books, fmt.Errorf("order validation failed while listing bookmarks: %w", err)
 		}
 
 		if err := validateQuery(options.query); err != nil {
-			return books, err
+			return books, fmt.Errorf("query validation failed while listing bookmarks: %w", err)
 		}
 
-		return getBooksDB(tx, getBooksDBArgs{
+		books, err := getBooksDB(tx, getBooksDBArgs{
 			includeBooks:   options.includeBookmarks,
 			includeFolders: options.includeFolders,
 			parentID:       options.parentID,
@@ -115,5 +119,10 @@ func ListBooks(options listBooksOptions) ([]Book, error) {
 			direction:      options.direction,
 			first:          options.first,
 		})
+		if err != nil {
+			return books, fmt.Errorf("error while listing bookmarks: %w", err)
+		}
+
+		return books, nil
 	})
 }
diff --git a/lib/list_tags.go b/lib/list_tags.go
index d276f8a..dade701 100644
--- a/lib/list_tags.go
+++ b/lib/list_tags.go
@@ -1,5 +1,9 @@
 package lib
 
+import (
+	"fmt"
+)
+
 // listTagsOptions are the optional arguments for ListTags.
 type listTagsOptions struct {
 	db        NullString
@@ -47,22 +51,27 @@ func ListTags(options listTagsOptions) ([]string, error) {
 		tags := make([]string, 0)
 
 		if err := validateFirst(options.first); err != nil {
-			return tags, err
+			return tags, fmt.Errorf("first validation failed while listing tags: %w", err)
 		}
 
 		if err := validateDirection(options.direction); err != nil {
-			return tags, err
+			return tags, fmt.Errorf("direction validation failed while listing tags: %w", err)
 		}
 
 		if err := validateQuery(options.query); err != nil {
-			return tags, err
+			return tags, fmt.Errorf("query validation failed while listing tags: %w", err)
 		}
 
-		return getTagsDB(tx, getTagsDBArgs{
+		tags, err := getTagsDB(tx, getTagsDBArgs{
 			query:     options.query,
 			after:     options.after,
 			direction: options.direction,
 			first:     options.first,
 		})
+		if err != nil {
+			return tags, fmt.Errorf("error while listing tags: %w", err)
+		}
+
+		return tags, nil
 	})
 }
diff --git a/lib/remove_book.go b/lib/remove_book.go
index d61f3a7..3c7a8cf 100644
--- a/lib/remove_book.go
+++ b/lib/remove_book.go
@@ -1,5 +1,9 @@
 package lib
 
+import (
+	"fmt"
+)
+
 // removeBookOptions are the optional arguments for RemoveBook.
 type removeBookOptions struct {
 	db NullString
@@ -19,7 +23,7 @@ func (o *removeBookOptions) WithDB(db string) {
 func RemoveBook(id string, options removeBookOptions) (err error) {
 	return execWithTransaction(options.db, connectDB, func(tx transaction) error {
 		if err := validateBookID(tx, id); err != nil {
-			return err
+			return fmt.Errorf("bookmark ID validation failed while removing bookmark: %w", err)
 		}
 
 		books, err := getBooksDB(tx, getBooksDBArgs{
@@ -27,20 +31,20 @@ func RemoveBook(id string, options removeBookOptions) (err error) {
 			includeBooks: true,
 		})
 		if err != nil {
-			return err
+			return fmt.Errorf("error getting bookmarks while removing bookmark: %w", err)
 		}
 		book := books[0]
 
 		if err = unlinkTagsDB(tx, book.ID, book.Tags); err != nil {
-			return err
+			return fmt.Errorf("error unlinking tags while removing bookmark: %w", err)
 		}
 
 		if err = removeBookDB(tx, book.ID); err != nil {
-			return err
+			return fmt.Errorf("error while removing bookmark: %w", err)
 		}
 
 		if err = cleanOrphanedTagsDB(tx, book.Tags); err != nil {
-			return err
+			return fmt.Errorf("error cleaning orphaned tags while removing bookmark: %w", err)
 		}
 
 		return nil
diff --git a/lib/remove_folder.go b/lib/remove_folder.go
index d44c7f9..55aac0d 100644
--- a/lib/remove_folder.go
+++ b/lib/remove_folder.go
@@ -1,6 +1,8 @@
 package lib
 
 import (
+	"fmt"
+
 	"github.com/samber/lo"
 )
 
@@ -23,30 +25,30 @@ func (o *removeFolderOptions) WithDB(db string) {
 func RemoveFolder(id string, options removeFolderOptions) error {
 	return execWithTransaction(options.db, connectDB, func(tx transaction) error {
 		if err := validateParentID(tx, NullStringFrom(id)); err != nil {
-			return err
+			return fmt.Errorf("parent ID validation failed while removing folder: %w", err)
 		}
 
 		bookOrFolders, err := getParentAndChildren(tx, id)
 		if err != nil {
-			return err
+			return fmt.Errorf("error getting folder and children while removing folder: %w", err)
 		}
 
 		for _, bookOrFolder := range lo.Reverse(bookOrFolders) {
 			if !bookOrFolder.IsFolder {
 				if err = unlinkTagsDB(tx, bookOrFolder.ID, bookOrFolder.Tags); err != nil {
-					return err
+					return fmt.Errorf("error unlinking tags while removing folder: %w", err)
 				}
 
 				if err = removeBookDB(tx, bookOrFolder.ID); err != nil {
-					return err
+					return fmt.Errorf("error remmoving bookmark while removing folder: %w", err)
 				}
 
 				if err = cleanOrphanedTagsDB(tx, bookOrFolder.Tags); err != nil {
-					return err
+					return fmt.Errorf("error cleaning orphaned tags while removing folder: %w", err)
 				}
 			} else {
 				if err = removeFolderDB(tx, bookOrFolder.ID); err != nil {
-					return err
+					return fmt.Errorf("error while removing folder: %w", err)
 				}
 			}
 		}
diff --git a/lib/remove_tags.go b/lib/remove_tags.go
index 5744865..3c52e5e 100644
--- a/lib/remove_tags.go
+++ b/lib/remove_tags.go
@@ -1,6 +1,8 @@
 package lib
 
 import (
+	"fmt"
+
 	"github.com/samber/lo"
 )
 
@@ -29,7 +31,7 @@ func RemoveTags(id string, tags []string, options removeTagsOptions) (Book, erro
 			includeBooks: true,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error getting bookmarks while removing tags: %w", err)
 		}
 
 		if len(books) != 1 || books[0].IsFolder {
@@ -43,11 +45,11 @@ func RemoveTags(id string, tags []string, options removeTagsOptions) (Book, erro
 		}
 
 		if err = unlinkTagsDB(tx, books[0].ID, tags); err != nil {
-			return book, err
+			return book, fmt.Errorf("error unlinking tags while removing tags: %w", err)
 		}
 
 		if err = cleanOrphanedTagsDB(tx, tags); err != nil {
-			return book, err
+			return book, fmt.Errorf("error cleaning orphaned tags while removing tags: %w", err)
 		}
 
 		books, err = getBooksDB(tx, getBooksDBArgs{
@@ -55,7 +57,7 @@ func RemoveTags(id string, tags []string, options removeTagsOptions) (Book, erro
 			includeBooks: true,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error getting bookmarks while removing tags: %w", err)
 		}
 
 		return books[0], nil
diff --git a/lib/transaction.go b/lib/transaction.go
index 71a6135..463c157 100644
--- a/lib/transaction.go
+++ b/lib/transaction.go
@@ -36,13 +36,14 @@ type queryTxFn[T any] func(transaction) (T, error)
 func queryWithTransaction[T any](inputPath NullString, connectFn connectDBFn, queryFn queryTxFn[T]) (val T, err error) {
 	db, err := connectFn(inputPath)
 	if err != nil {
+		err = fmt.Errorf("error connecting to database while querying with a transaction: %w", err)
 		return
 	}
 	defer db.Close()
 
 	tx, err := db.Begin()
 	if err != nil {
-		err = fmt.Errorf("%w: %w", ErrUnexpected, err)
+		err = fmt.Errorf("error beginning transaction while querying with a transaction: %w", err)
 		return
 	}
 
@@ -60,13 +61,17 @@ func queryWithTransaction[T any](inputPath NullString, connectFn connectDBFn, qu
 			// all good, commit
 			err = tx.Commit()
 			if err != nil {
-				err = fmt.Errorf("%w: %w", ErrUnexpected, err)
+				err = fmt.Errorf("error committing transaction while querying with a transaction: %w", err)
 			}
 		}
 	}()
 
 	val, err = queryFn(tx)
-	return val, err
+	if err != nil {
+		return val, fmt.Errorf("error while querying with a transaction: %w", err)
+	}
+
+	return val, nil
 }
 
 // QueryTxFn is a function that operates on a transaction which doesn't return results.
@@ -78,13 +83,14 @@ type execTxFn func(transaction) error
 func execWithTransaction(inputPath NullString, connectFn connectDBFn, execFn execTxFn) (err error) {
 	db, err := connectFn(inputPath)
 	if err != nil {
+		err = fmt.Errorf("error connecting to database while executing with a transaction: %w", err)
 		return
 	}
 	defer db.Close()
 
 	tx, err := db.Begin()
 	if err != nil {
-		err = fmt.Errorf("%w: %w", ErrUnexpected, err)
+		err = fmt.Errorf("error beginning transaction while executing with a transaction: %w", err)
 		return
 	}
 
@@ -102,13 +108,17 @@ func execWithTransaction(inputPath NullString, connectFn connectDBFn, execFn exe
 			// all good, commit
 			err = tx.Commit()
 			if err != nil {
-				err = fmt.Errorf("%w: %w", ErrUnexpected, err)
+				err = fmt.Errorf("error committing transaction while executing with a transaction: %w", err)
 			}
 		}
 	}()
 
 	err = execFn(tx)
-	return err
+	if err != nil {
+		return fmt.Errorf("error while executing with a transaction: %w", err)
+	}
+
+	return nil
 }
 
 // queryWithDB creates a scope for for functions that operate on a database connection which return results.
@@ -119,11 +129,16 @@ func queryWithDB[T any](inputPath NullString, connectFn connectDBFn, queryFn que
 
 	db, err := connectFn(inputPath)
 	if err != nil {
-		return val, err
+		return val, fmt.Errorf("error connecting to database while querying with database: %w", err)
 	}
 	defer db.Close()
 
-	return queryFn(db)
+	val, err = queryFn(db)
+	if err != nil {
+		return val, fmt.Errorf("error while querying with database: %w", err)
+	}
+
+	return val, nil
 }
 
 // connectDBFn is a function that connects to SQLite database
@@ -133,25 +148,25 @@ type connectDBFn func(inputPath NullString) (*sql.DB, error)
 func connectDB(inputPath NullString) (*sql.DB, error) {
 	config, err := GetConfig()
 	if err != nil && !errors.Is(err, ErrConfigMissing) {
-		return nil, err
+		return nil, fmt.Errorf("error getting config wile connecting to database: %w", err)
 	}
 
 	dbLocation, err := getDatabasePath(inputPath, config.DB, runtime.GOOS, os.MkdirAll, os.UserHomeDir, filepath.Join)
 	if err != nil {
-		return nil, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return nil, fmt.Errorf("error getting database location wile connecting to database: %w", err)
 	}
 
 	db, err := sql.Open("sqlite3", dbLocation)
 	if err != nil {
-		return nil, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return nil, fmt.Errorf("error while connecting to database: %w", err)
 	}
 
 	if err := configureDB(db); err != nil {
-		return nil, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return nil, fmt.Errorf("error configuring database wile connecting to database: %w", err)
 	}
 
 	if err := migrateDB(db); err != nil {
-		return nil, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return nil, fmt.Errorf("error applying migrations to database wile connecting to database: %w", err)
 	}
 
 	return db, nil
@@ -162,11 +177,11 @@ func connectDB(inputPath NullString) (*sql.DB, error) {
 // - Enforce foreign keys.
 func configureDB(db *sql.DB) error {
 	if _, err := db.Exec("PRAGMA journal_mode=WAL"); err != nil {
-		return err
+		return fmt.Errorf("error turning WAL mode on while configuring database: %w", err)
 	}
 
 	if _, err := db.Exec("PRAGMA foreign_keys=on"); err != nil {
-		return err
+		return fmt.Errorf("error turning foreign key checking on while configuring database: %w", err)
 	}
 
 	return nil
@@ -178,11 +193,11 @@ func migrateDB(db *sql.DB) error {
 	goose.SetLogger(goose.NopLogger())
 
 	if err := goose.SetDialect("sqlite3"); err != nil {
-		return err
+		return fmt.Errorf("error setting dialect while applying migrations: %w", err)
 	}
 
 	if err := goose.Up(db, "migrations"); err != nil {
-		return err
+		return fmt.Errorf("error while applying migrations: %w", err)
 	}
 
 	return nil
@@ -194,19 +209,19 @@ func query[T any](tx transaction, q *bqb.Query) ([]T, error) {
 
 	sql, args, err := q.ToSql()
 	if err != nil {
-		return nil, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return nil, fmt.Errorf("error building query while querying: %w", err)
 	}
 
 	rows, err := tx.Query(sql, args...)
 	if err != nil {
-		return nil, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return nil, fmt.Errorf("error while querying: %w", err)
 	}
 
 	defer rows.Close()
 
 	err = scan.RowsStrict(&results, rows)
 	if err != nil {
-		return nil, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return nil, fmt.Errorf("error building results while querying: %w", err)
 	}
 
 	return results, nil
@@ -216,11 +231,11 @@ func query[T any](tx transaction, q *bqb.Query) ([]T, error) {
 func exec(tx transaction, q *bqb.Query) error {
 	sql, args, err := q.ToSql()
 	if err != nil {
-		return fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return fmt.Errorf("error building query while executing: %w", err)
 	}
 
 	if _, err = tx.Exec(sql, args...); err != nil {
-		return fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return fmt.Errorf("error while executing: %w", err)
 	}
 
 	return nil
@@ -230,12 +245,12 @@ func exec(tx transaction, q *bqb.Query) error {
 func count(tx transaction, q *bqb.Query) (int, error) {
 	sql, args, err := q.ToSql()
 	if err != nil {
-		return 0, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return 0, fmt.Errorf("error building query while counting: %w", err)
 	}
 
 	var count = 0
 	if err = tx.QueryRow(sql, args...).Scan(&count); err != nil {
-		return 0, fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return 0, fmt.Errorf("error while counting: %w", err)
 	}
 
 	return count, nil
diff --git a/lib/update_book.go b/lib/update_book.go
index d9624c3..de99e7f 100644
--- a/lib/update_book.go
+++ b/lib/update_book.go
@@ -1,5 +1,9 @@
 package lib
 
+import (
+	"fmt"
+)
+
 // updateBookOptions are the optional arguments for UpdateBook.
 type updateBookOptions struct {
 	db          NullString
@@ -55,7 +59,7 @@ func UpdateBook(id string, options updateBookOptions) (Book, error) {
 		var book Book
 
 		if err := validateBookID(tx, id); err != nil {
-			return book, err
+			return book, fmt.Errorf("bookmark ID validation failed while updating bookmark: %w", err)
 		}
 
 		if !options.name.Dirty && !options.url.Dirty && !options.description.Dirty && !options.parentID.Dirty {
@@ -64,25 +68,25 @@ func UpdateBook(id string, options updateBookOptions) (Book, error) {
 
 		if options.name.Dirty {
 			if err := validateName(options.name); err != nil {
-				return book, err
+				return book, fmt.Errorf("name validation failed while updating bookmark: %w", err)
 			}
 		}
 
 		if options.url.Dirty {
 			if err := validateURL(options.url); err != nil {
-				return book, err
+				return book, fmt.Errorf("URL validation failed while updating bookmark: %w", err)
 			}
 		}
 
 		if options.description.Dirty {
 			if err := validateDescription(options.description); err != nil {
-				return book, err
+				return book, fmt.Errorf("description validation failed while updating bookmark: %w", err)
 			}
 		}
 
 		if options.parentID.Dirty {
 			if err := validateParentID(tx, options.parentID); err != nil {
-				return book, err
+				return book, fmt.Errorf("parent ID validation failed while updating bookmark: %w", err)
 			}
 		}
 
@@ -92,7 +96,7 @@ func UpdateBook(id string, options updateBookOptions) (Book, error) {
 			description: options.description,
 			parentID:    options.parentID,
 		}); err != nil {
-			return book, err
+			return book, fmt.Errorf("error while updating bookmark: %w", err)
 		}
 
 		books, err := getBooksDB(tx, getBooksDBArgs{
@@ -100,7 +104,7 @@ func UpdateBook(id string, options updateBookOptions) (Book, error) {
 			includeBooks: true,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error getting bookmarks while updating bookmark: %w", err)
 		}
 
 		return books[0], nil
diff --git a/lib/update_folder.go b/lib/update_folder.go
index f52245a..4a828f3 100644
--- a/lib/update_folder.go
+++ b/lib/update_folder.go
@@ -1,5 +1,9 @@
 package lib
 
+import (
+	"fmt"
+)
+
 // updateFolderOptions are the optional arguments for UpdateFolder.
 type updateFolderOptions struct {
 	db       NullString
@@ -38,7 +42,7 @@ func UpdateFolder(id string, options updateFolderOptions) (Book, error) {
 		var book Book
 
 		if err := validateParentID(tx, NullStringFrom(id)); err != nil {
-			return book, err
+			return book, fmt.Errorf("bookmark ID validation failed while updating folder: %w", err)
 		}
 
 		if !options.name.Dirty && !options.parentID.Dirty {
@@ -47,13 +51,13 @@ func UpdateFolder(id string, options updateFolderOptions) (Book, error) {
 
 		if options.name.Dirty {
 			if err := validateName(options.name); err != nil {
-				return book, err
+				return book, fmt.Errorf("name validation failed while updating folder: %w", err)
 			}
 		}
 
 		if options.parentID.Dirty {
 			if err := validateParentID(tx, options.parentID); err != nil {
-				return book, err
+				return book, fmt.Errorf("parent ID validation failed while updating folder: %w", err)
 			}
 		}
 
@@ -61,7 +65,7 @@ func UpdateFolder(id string, options updateFolderOptions) (Book, error) {
 			name:     options.name,
 			parentID: options.parentID,
 		}); err != nil {
-			return book, err
+			return book, fmt.Errorf("error while updating folder: %w", err)
 		}
 
 		books, err := getBooksDB(tx, getBooksDBArgs{
@@ -69,7 +73,7 @@ func UpdateFolder(id string, options updateFolderOptions) (Book, error) {
 			includeFolders: true,
 		})
 		if err != nil {
-			return book, err
+			return book, fmt.Errorf("error geting bookmarks while updating folder: %w", err)
 		}
 
 		return books[0], nil
diff --git a/lib/validators.go b/lib/validators.go
index a302f09..d08aece 100644
--- a/lib/validators.go
+++ b/lib/validators.go
@@ -75,9 +75,9 @@ func validateTags(tags []string, existingTags []string) error {
 		return ErrDuplicateTag
 	}
 
-	r, e := regexp.Compile(`^[a-zA-Z0-9\-_]*$`)
-	if e != nil {
-		return e
+	r, err := regexp.Compile(`^[a-zA-Z0-9\-_]*$`)
+	if err != nil {
+		return fmt.Errorf("error compiling regex while validating tags: %w", err)
 	}
 
 	for _, tag := range tags {
@@ -156,7 +156,7 @@ func validateQuery(query NullString) error {
 func validateBookID(tx transaction, ID string) error {
 	exists, err := bookFolderExistsDB(tx, ID, false)
 	if err != nil {
-		return fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return fmt.Errorf("error checking if bookmark exists while validating bookmark ID")
 	}
 
 	if !exists {
@@ -175,7 +175,7 @@ func validateParentID(tx transaction, parentID NullString) error {
 
 	exists, err := bookFolderExistsDB(tx, parentID.String, true)
 	if err != nil {
-		return fmt.Errorf("%w: %w", ErrUnexpected, err)
+		return fmt.Errorf("error checking if folder exists while validating parent ID")
 	}
 
 	if !exists {