Octoprint not starting after Trixie upgrade

Didel · 23 November 2025 22:25

Creating a bug report/issue

I have searched the existing open and closed issues

Required Information

DietPi version | cat /boot/dietpi/.version

G_DIETPI_VERSION_CORE=9
G_DIETPI_VERSION_SUB=19
G_DIETPI_VERSION_RC=2
G_GITBRANCH=‘master’
G_GITOWNER=‘MichaIng’
Distro version | echo $G_DISTRO_NAME $G_RASPBIAN

trixie
Kernel version | uname --all

Linux DietPi 6.12.57-current-rockchip64 #1 SMP PREEMPT Sun Nov 2 13:15:23 UTC 2025 aarch64 GNU/Linux
Architecture | dpkg --print-architecture

arm64
SBC model | echo $G_HW_MODEL_NAME or (EG: RPi3)

ROCK 4 (aarch64)
Power supply used | (EG: 5V 1A RAVpower)

USB-C power supply
SD card used | (EG: SanDisk ultra)

Onboard EMMC

Additional Information (if applicable)

Software title | (EG: Nextcloud)

Octoprint
Was the software title installed freshly or updated/migrated?

Octoprint is the same, OS upgraded from bookworm to trixie
Can this issue be replicated on a fresh installation of DietPi?

Not tried…

← If you sent a “dietpi-bugreport”, please paste the ID here →
Bug report ID | echo $G_HW_UUID

323a7fd9-08f7-441b-9787-0fb6743c0df7

Steps to reproduce

Have a working dietpi and Octoprint install on bookworm (with no available updates)
Upgrade OS to trixie by running

sudo bash -c “$(curl -sSf ‘https://raw.githubusercontent.com/MichaIng/DietPi/dev/.meta/dietpi-trixie-upgrade’)”
Follow onscreen instructions and assure no errors are present
Wait until ‘You have successfully been upgraded to Trixie’ (or similar) message appears and all install steps are done.
Reboot device
Octoprint won’t start

Expected behaviour

Octoprint starts as usual automatically after a (re)boot or after manually running octoprint serve

Actual behaviour

Octoprint is not started automatically, and starting it manually throws an error.

Extra details

the following error is shown:

root@DietPi:~# octoprint serve
2025-11-23 23:21:57,341 - octoprint.startup - CRITICAL - There was a fatal error initializing OctoPrint:
Traceback (most recent call last):
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/init.py”, line 96, in init_platform
settings = init_settings(basedir, configfile, overlays=overlays)
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/init.py”, line 209, in init_settings
from octoprint.settings import InvalidSettings, settings
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/settings/init.py”, line 36, in
from octoprint.schema.config import Config
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/schema/config/init.py”, line 7, in
from octoprint.vendor.with_attrs_docs import with_attrs_docs
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/vendor/with_attrs_docs.py”, line 7, in
from .class_doc import extract_docs_from_cls_obj
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/vendor/class_doc.py”, line 14, in
import more_itertools as mitertools
ModuleNotFoundError: No module named ‘more_itertools’

The above exception was the direct cause of the following exception:

Traceback (most recent call last):
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/cli/server.py”, line 112, in run_server
components = init_platform(
basedir,
…<10 lines>…
disable_color=disable_color,
)
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/init.py”, line 98, in init_platform
raise FatalStartupError(“Could not initialize settings manager”, cause=ex) from ex
octoprint.FatalStartupError: Could not initialize settings manager: No module named ‘more_itertools’
Traceback (most recent call last):
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/init.py”, line 96, in init_platform
settings = init_settings(basedir, configfile, overlays=overlays)
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/init.py”, line 209, in init_settings
from octoprint.settings import InvalidSettings, settings
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/settings/init.py”, line 36, in
from octoprint.schema.config import Config
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/schema/config/init.py”, line 7, in
from octoprint.vendor.with_attrs_docs import with_attrs_docs
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/vendor/with_attrs_docs.py”, line 7, in
from .class_doc import extract_docs_from_cls_obj
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/vendor/class_doc.py”, line 14, in
import more_itertools as mitertools
ModuleNotFoundError: No module named ‘more_itertools’

The above exception was the direct cause of the following exception:

Traceback (most recent call last):
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/cli/server.py”, line 112, in run_server
components = init_platform(
basedir,
…<10 lines>…
disable_color=disable_color,
)
File “/mnt/dietpi_userdata/octoprint/.local/lib/python3.13/site-packages/octoprint/init.py”, line 98, in init_platform
raise FatalStartupError(“Could not initialize settings manager”, cause=ex) from ex
octoprint.FatalStartupError: Could not initialize settings manager: No module named ‘more_itertools’

There was a fatal error initializing OctoPrint: Could not initialize settings manager: No module named ‘more_itertools’

Thanks in advance for your help!

MichaIng · 23 November 2025 23:44

You probably installed a plugin which requires this additional module. Please try this:

sudo -u octoprint pip3 install -U --user more_itertools

But I’m running test installs to assure it is no core dependency that has been missed to be declared as such in OctoPrint or one of its dependencies: DietPi-Software test · MichaIng/DietPi@77e6c78 · GitHub

The import is actually done here:

github.com/danields761/class-doc

class_doc.py

master


      
          import inspect
          import itertools
          import string
          import textwrap
          import tokenize
          from typing import Dict, List, Optional, Union, Iterator, Any
          
          import more_itertools as mitertools
          
          import ast
          
          
          def _test_advanced_ast_presence() -> bool:
              return len({'end_lineno', 'end_col_offset'} & set(ast.ClassDef._attributes)) > 0
          
          
          UniversalAssign = Union[ast.Assign, ast.AnnAssign]

And that package declares it as dependency:

github.com/danields761/class-doc

pyproject.toml

master


      
              "Programming Language :: Python :: 3.9",
              "Operating System :: OS Independent",
              "License :: OSI Approved :: MIT License",
              "Topic :: Software Development :: Libraries :: Python Modules",
              "Topic :: Internet",
          ]
          
          
          [tool.poetry.dependencies]
          python = "^3.6"
          more-itertools = ">=5.0.0"
          
          [tool.poetry.dev-dependencies]
          pytest = "^5.1.2"
          tox = "^3.21.4"
          
          [build-system]
          requires = ["poetry>=0.12"]
          build-backend = "poetry.masonry.api"
          
          [tool.black]

OctoPrint vendors it in:

github.com/OctoPrint/OctoPrint

src/octoprint/vendor/class_doc.py

dev


      
          # vendored for compatibility reasons
          
          import inspect
          import itertools
          import string
          import sys
          import textwrap
          import tokenize
          from typing import Dict, List, Optional, Union, Iterator, Any
          
          import more_itertools as mitertools
          
          import ast
          
          if sys.version_info >= (3, 8, 0):
              AST_CONSTANT_TYPE = ast.Constant
              AST_CONSTANT_VALUE = lambda x: x.value
          else:  # Python 3.7
              AST_CONSTANT_TYPE = ast.Str
              AST_CONSTANT_VALUE = lambda x: x.s

But does not declare it as dependency:

github.com/OctoPrint/OctoPrint

pyproject.toml

dev


      
              "Programming Language :: Python :: 3.12",
              "Programming Language :: Python :: 3.13",
              "Programming Language :: Python :: 3 :: Only",
              "Programming Language :: Python :: Implementation :: CPython",
              "Programming Language :: JavaScript",
              "Topic :: Printing",
          ]
          
          requires-python = ">=3.9, <3.14"
          
          dependencies = [
              # bundled plugins
              "OctoPrint-FileCheck>=2024.11.12",
              "OctoPrint-FirmwareCheck>=2021.10.11",
              "OctoPrint-PiSupport>=2023.10.10",
          
              # core deps
              "argon2-cffi>=23.1.0",
              "Babel>=2.16,<2.17",  # breaking changes can happen on minor version increases
              "cachelib>=0.13.0,<0.14",
              "Click>=8.1.8,!=8.2.0,<9",  # 8.2.0 has broken flags, see pallets/click#2894

My install tests all succeed, so looks like this is called only in certain conditions.

It is imported here:

github.com/OctoPrint/OctoPrint

src/octoprint/vendor/with_attrs_docs.py

dev


      
          # Based on pydantic-settings version 0.2.5 by Daniel Daniels, licensed under MIT
          #
          # See <https://github.com/danields761/pydantic-settings>
          
          from typing import Type
          
          from .class_doc import extract_docs_from_cls_obj
          from pydantic import BaseModel
          from pydantic import __version__ as pydantic_version
          
          if pydantic_version.startswith("1."):
              # pydantic 1.x
              def apply_attributes_docs(
                  model: Type[BaseModel], override_existing: bool = True
              ) -> None:
                  """
                  Apply model attributes documentation in-place. Resulted docs are placed

That however is imported at a lot of places: Code search results · GitHub

Hmm, in my logs the module is actually installed:

Collecting more-itertools>=10.5.0 (from octoprint)
  Downloading more_itertools-10.8.0-py3-none-any.whl.metadata (39 kB)

Ahh oh OctoPrint DOES define it as dependency, just with dash instead of underscore (which both works):

github.com/OctoPrint/OctoPrint

pyproject.toml

dev


      
          "tornado>=6.5,<6.6",
          "watchdog>=6,<7",
          "websocket-client>=1.8.0,<1.9",  # breaking changes can happen on patch version increases, changelog incomplete
          "werkzeug>=3.1.3,<3.2",  # breaking changes can happen on minor version increases
          "wrapt>=1.17.2,<1.18",
          "zeroconf>=0.141,<0.142",  # breaking changes can happen on minor version increases (despite semantic versioning)
          "zipstream-ng>=1.8.0,<2.0.0",
          
          # vendored deps
          "blinker>=1.9.0,<1.10.0",  # dependency of flask_principal
          "more-itertools>=10.6.0",  # dependency of class-doc
          "regex",  # dependency of awesome-slugify
          "unidecode",  # dependency of awesome-slugify
          
          # plugin deps
          # "OctoPrint-Setuptools>=1.0.3",  # makes sure plugins can import this on setup.py based install
          "future",  # some plugins might still depend on this but not in their own requirements
          "wheel",  # makes sure plugins can be built as wheels in OctoPrint's venv, see #4682
          
          # OS specific deps
          "appdirs ; sys_platform=='darwin'"

Okay, so why was it not installed in your case?

If you did not install it manually yet, what does this return?

sudo -u octoprint pip3 freeze --user