Error when upgrading from 1.3.10 to 1.4.0 via "Update Now" button

I am running OctoPi on a Raspberry Pi 2 (I think). I've been running it for a couple of years now, upgrading along the way as needed and the upgrade has always worked fine. When I got the notification about 1.4.0, I clicked "Update now" but this time I got an error.

OctoPrint version : 1.3.10
OctoPi version : 0.14.0

I ran sudo apt update and sudo apt upgrade to make sure the issue wasn't related to an out-of-date package, but I still get an error after that.

Here is the error message from the UI:

Updating, please wait.
+++++++++++++++++++++++++++++++
Now updating OctoPrint to 1.4.0
+++++++++++++++++++++++++++++++
/home/pi/oprint/bin/python -m pip install https://github.com/foosel/OctoPrint/archive/1.4.0.zip --no-cache-dir
Collecting https://github.com/foosel/OctoPrint/archive/1.4.0.zip
Downloading https://github.com/foosel/OctoPrint/archive/1.4.0.zip (5.5MB)
Complete output from command python setup.py egg_info:
Traceback (most recent call last):
File "<string>", line 1, in <module>
File "/tmp/pip-Zh9bHf-build/setup.py", line 277, in <module>
setup(**params())
File "/usr/lib/python2.7/distutils/core.py", line 111, in setup
_setup_distribution = dist = klass(attrs)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/dist.py", line 262, in __init__
self.fetch_build_eggs(attrs['setup_requires'])
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/dist.py", line 287, in fetch_build_eggs
replace_conflicting=True,
File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 631, in resolve
dist = best[req.key] = env.best_match(req, ws, installer)
File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 874, in best_match
return self.obtain(req, installer)
File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 886, in obtain
return installer(requirement)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/dist.py", line 338, in fetch_build_egg
return cmd.easy_install(req)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/command/easy_install.py", line 636, in easy_install
return self.install_item(spec, dist.location, tmpdir, deps)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/command/easy_install.py", line 666, in install_item
dists = self.install_eggs(spec, download, tmpdir)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/command/easy_install.py", line 856, in install_eggs
return self.build_and_install(setup_script, setup_base)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/command/easy_install.py", line 1078, in build_and_install
self.run_setup(setup_script, setup_base, args)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/command/easy_install.py", line 1063, in run_setup
run_setup(setup_script, args)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/sandbox.py", line 68, in run_setup
DirectorySandbox(setup_dir).run(runner)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/sandbox.py", line 114, in run
return func()
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/sandbox.py", line 67, in runner
_execfile(setup_script, ns)
File "/home/pi/oprint/local/lib/python2.7/site-packages/setuptools/sandbox.py", line 43, in _execfile
exec(code, globals, locals)
File "/tmp/easy_install-jeHe2h/Markdown-3.1.1/setup.py", line 46, in <module>
"markdown>=3.1,<3.2",
File "/tmp/easy_install-jeHe2h/Markdown-3.1.1/setup.py", line 36, in get_version
File "markdown/__meta__.py", line 26, in <module>
ImportError: No module named extern
----------------------------------------
Command "python setup.py egg_info" failed with error code 1 in /tmp/pip-Zh9bHf-build/
You are using pip version 9.0.1, however version 20.0.2 is available.
You should consider upgrading via the 'pip install --upgrade pip' command.
The update did not finish successfully. Please consult <code>octoprint.log</code> and <code>plugin_softwareupdate_console.log</code> for details.

Here is the octoprint log:

$ more .octoprint/logs/octoprint.log
2020-04-08 17:01:42,664 - octoprint.util.connectivity_checker - INFO - Connectivity changed from offline to online
2020-04-08 17:01:42,672 - octoprint.plugin.core - INFO - Found 20 plugin(s) providing 20 mixin implementations, 26 hook handlers
2020-04-08 17:01:42,679 - octoprint.server.heartbeat - INFO - Starting server heartbeat, 900.0s interval
2020-04-08 17:01:42,700 - octoprint.server - INFO - --- Log roll over detected ---------------------------------------------------
2020-04-08 17:01:42,701 - octoprint.server - INFO - OctoPrint 1.3.10
2020-04-08 17:01:42,705 - octoprint.plugin.core - INFO - 20 plugin(s) registered with the system:
|  Action Command Prompt Support (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/action_command_prompt
|  Announcement Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/announcements
|  Anonymous Usage Tracking (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/tracking
|  Application Keys Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/appkeys
|  Backup & Restore (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/backup
|  Core Wizard (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/corewizard
|  CuraEngine (<= 15.04) (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/cura
|  Detailed Progress Plugin (0.1.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_detailedprogress
|  Discovery (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/discovery
|  Display ETA (1.0.2) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_eta
|  Force Login (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/forcelogin
|  Fullscreen Plugin (0.0.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_fullscreen
|  Logging (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/logging
|  Octolapse (v0.3.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_octolapse
|  Pi Support Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pi_support
|  Plugin Manager (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pluginmanager
|  Printer Safety Check (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/printer_safety_check
|  Software Update (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate
|  STL Viewer (0.4.1) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_stlviewer
|  Virtual Printer (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/virtual_printer
2020-04-08 17:01:42,716 - octoprint.environment - ERROR - Unexpected error while detecting environment
Traceback (most recent call last):
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/environment.py", line 46, in run_detection
    plugin_result = self._detect_from_plugins()
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/environment.py", line 123, in _detect_from_plugins
    "environment data from plugin {}".format(implementation._identifier))
AttributeError: 'PiSupportPlugin' object has no attribute '_identifier'
2020-04-08 17:01:42,720 - octoprint.environment - ERROR - Error logging detected environment
Traceback (most recent call last):
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/environment.py", line 136, in log_detected_environment
    _log(self._format())
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/environment.py", line 151, in _format
    return u"Detected environment is Python {} under {} ({}). Details:\n{}".format(environment["python"]["version"],
KeyError: 'python'
2020-04-08 17:01:42,722 - octoprint.server - INFO - ------------------------------------------------------------------------------
2020-04-08 17:01:42,822 - octoprint.server - INFO - Intermediary server started
2020-04-08 17:01:42,823 - octoprint.plugin.core - INFO - Loading plugins from /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins, /home/pi/.octoprint/plugins and installed plugin packages...
2020-04-08 17:01:43,548 - octoprint.plugin.core - INFO - Found 20 plugin(s) providing 20 mixin implementations, 26 hook handlers
2020-04-08 17:01:43,643 - octoprint.filemanager.storage - INFO - Initializing the file metadata for /home/pi/.octoprint/uploads...
2020-04-08 17:01:45,237 - octoprint.filemanager.storage - INFO - ... file metadata for /home/pi/.octoprint/uploads initialized successfully.
2020-04-08 17:01:45,338 - octoprint.plugins.tracking - INFO - Initialized anonymous tracking
2020-04-08 17:01:45,598 - octoprint.plugins.softwareupdate - INFO - Loaded version cache from disk
2020-04-08 17:01:51,617 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python -m pip" as command to invoke pip
2020-04-08 17:01:55,771 - octoprint.util.pip - INFO - Version of pip is 9.0.1
2020-04-08 17:01:55,773 - octoprint.util.pip - INFO - pip installs to /home/pi/oprint/lib/python2.7/site-packages (writable -> yes), --user flag needed -> no, virtual env -> yes
2020-04-08 17:01:55,774 - octoprint.util.pip - INFO - ==> pip ok -> yes
2020-04-08 17:01:55,786 - octoprint.plugin.core - INFO - Initialized 20 plugin implementation(s)
2020-04-08 17:01:55,807 - octoprint.plugin.core - INFO - 20 plugin(s) registered with the system:
|  Action Command Prompt Support (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/action_command_prompt
|  Announcement Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/announcements
|  Anonymous Usage Tracking (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/tracking
|  Application Keys Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/appkeys
|  Backup & Restore (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/backup
|  Core Wizard (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/corewizard
|  CuraEngine (<= 15.04) (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/cura
|  Detailed Progress Plugin (0.1.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_detailedprogress
|  Discovery (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/discovery
|  Display ETA (1.0.2) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_eta
|  Force Login (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/forcelogin
|  Fullscreen Plugin (0.0.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_fullscreen
|  Logging (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/logging
|  Octolapse (v0.3.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_octolapse
|  Pi Support Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pi_support
|  Plugin Manager (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pluginmanager
|  Printer Safety Check (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/printer_safety_check
|  Software Update (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate
|  STL Viewer (0.4.1) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_stlviewer
|  Virtual Printer (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/virtual_printer
2020-04-08 17:01:55,810 - octoprint.environment - ERROR - Error logging detected environment
Traceback (most recent call last):
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/environment.py", line 136, in log_detected_environment
    _log(self._format())
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/environment.py", line 151, in _format
    return u"Detected environment is Python {} under {} ({}). Details:\n{}".format(environment["python"]["version"],
KeyError: 'python'
2020-04-08 17:01:55,832 - octoprint.server - INFO - Reset webasset folder /home/pi/.octoprint/generated/webassets...
2020-04-08 17:01:55,889 - octoprint.server - INFO - Reset webasset folder /home/pi/.octoprint/generated/.webassets-cache...
2020-04-08 17:01:55,933 - octoprint.plugins.octolapse - INFO - Octolapse is loading assets.
2020-04-08 17:01:56,576 - octoprint.server - INFO - Shutting down intermediary server...
2020-04-08 17:01:57,038 - octoprint.server - INFO - Intermediary server shut down
2020-04-08 17:01:57,046 - octoprint.events - INFO - Processing startup event, this is our first event
2020-04-08 17:01:57,047 - octoprint.events - INFO - Adding 1 events to queue that were held back before startup event
2020-04-08 17:01:57,063 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2020-04-08 17:01:57,152 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2020-04-08 17:01:57,455 - octoprint.util.comm - INFO - Changing monitoring state from "Offline" to "Detecting serial port"
2020-04-08 17:01:57,549 - octoprint.plugins.discovery - INFO - Registered 'OctoPrint instance on octopi' for _http._tcp
2020-04-08 17:01:57,741 - octoprint.plugins.discovery - INFO - Registered 'OctoPrint instance on octopi' for _octoprint._tcp
2020-04-08 17:01:57,786 - octoprint.util.comm - INFO - Changing monitoring state from "Detecting serial port" to "Opening serial port"
2020-04-08 17:01:57,830 - octoprint.plugins.discovery - INFO - Registered OctoPrint instance on octopi for SSDP
2020-04-08 17:01:57,857 - octoprint.util.comm - INFO - Changing monitoring state from "Opening serial port" to "Detecting baudrate"
2020-04-08 17:01:57,886 - octoprint.plugins.pi_support - WARNING - This Raspberry Pi is reporting problems that might lead to bad performance or errors caused by overheating or insufficient power.
!!! UNDERVOLTAGE REPORTED !!! Make sure that the power supply and power cable are capable of supplying enough voltage and current to your Pi.
2020-04-08 17:01:57,981 - octoprint.server - INFO - Listening on http://127.0.0.1:5000
2020-04-08 17:01:58,009 - octoprint.plugins.octolapse - INFO - Loading existing settings file from: /home/pi/.octoprint/data/octolapse/settings.json.
2020-04-08 17:01:58,689 - octoprint.plugins.announcements - INFO - Loaded channel _important from https://octoprint.org/feeds/important.xml in 1.4s
2020-04-08 17:01:59,002 - octoprint.util.comm - INFO - M110 detected, setting current line number to 0
2020-04-08 17:01:59,079 - octoprint.plugins.pluginmanager - INFO - Loaded plugin repository data from https://plugins.octoprint.org/plugins.json
2020-04-08 17:01:59,352 - octoprint.util.comm - INFO - Changing monitoring state from "Detecting baudrate" to "Operational"
2020-04-08 17:01:59,423 - octoprint.plugins.tracking - INFO - Sent tracking event system_throttled, payload: {'throttled_mask': 327685, 'throttled_voltage_now': True, 'throttled_voltage_past': True, 'throttled_overheat_now': False, 'thr
ottled_now': True, 'throttled_past': True, 'throttled_overheat_past': False}
2020-04-08 17:01:59,525 - octoprint.util.comm - INFO - M110 detected, setting current line number to 0
2020-04-08 17:02:00,466 - octoprint.util.comm - INFO - Printer reports firmware name "ANET_A8_20160525  http://www.anet3d.com/"
2020-04-08 17:02:00,473 - octoprint.util.comm - INFO - Detected Repetier firmware, enabling relevant features for issue free communication
2020-04-08 17:02:00,917 - octoprint.plugins.announcements - INFO - Loaded channel _important from https://octoprint.org/feeds/important.xml in 1.8s
2020-04-08 17:02:01,436 - octoprint.plugins.pluginmanager - INFO - Loaded plugin repository data from https://plugins.octoprint.org/plugins.json
2020-04-08 17:02:01,904 - octoprint.plugins.tracking - INFO - Sent tracking event printer_connected, payload: {u'printer_baudrate': 0, u'printer_port': 'AUTO', 'firmware_name': 'ANET_A8_20160525  http://www.anet3d.com/'}
2020-04-08 17:02:03,019 - octoprint.util.version - ERROR - Something is wrong with this compatibility string for OctoPrint: >=1.3.4+
Traceback (most recent call last):
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/util/version.py", line 109, in is_octoprint_compatible
    s = pkg_resources.Requirement.parse("OctoPrint" + octo_compat)
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 2793, in parse
    reqs = list(parse_requirements(s))
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 2721, in parse_requirements
    "version spec")
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 2697, in scan_list
    raise ValueError(msg, line, "at", line[p:])
ValueError: ("Expected ',' or end-of-list in", 'OctoPrint>=1.3.4+', 'at', '+')
2020-04-08 17:02:03,366 - octoprint.plugins.announcements - INFO - Loaded channel _releases from https://octoprint.org/feeds/releases.xml in 1.4s
2020-04-08 17:02:04,776 - octoprint.plugins.pluginmanager - INFO - Loaded plugin notices data from https://plugins.octoprint.org/notices.json
2020-04-08 17:02:05,621 - octoprint.plugins.announcements - INFO - Loaded channel _releases from https://octoprint.org/feeds/releases.xml in 1.6s
2020-04-08 17:02:06,166 - octoprint.util.version - ERROR - Something is wrong with this compatibility string for OctoPrint: >=1.3.4+
Traceback (most recent call last):
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/util/version.py", line 109, in is_octoprint_compatible
    s = pkg_resources.Requirement.parse("OctoPrint" + octo_compat)
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 2793, in parse
    reqs = list(parse_requirements(s))
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 2721, in parse_requirements
    "version spec")
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pkg_resources.py", line 2697, in scan_list
    raise ValueError(msg, line, "at", line[p:])
ValueError: ("Expected ',' or end-of-list in", 'OctoPrint>=1.3.4+', 'at', '+')
2020-04-08 17:02:06,302 - octoprint.plugins.pluginmanager - INFO - Loaded notice data from disk, was still valid
2020-04-08 17:02:11,113 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python -m pip" as command to invoke pip
2020-04-08 17:02:11,406 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python -m pip" as command to invoke pip
2020-04-08 17:02:12,432 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python -m pip" as command to invoke pip
2020-04-08 17:02:13,523 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python -m pip" as command to invoke pip
2020-04-08 17:02:13,950 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python -m pip" as command to invoke pip
2020-04-08 17:02:14,134 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python -m pip" as command to invoke pip
2020-04-08 17:02:14,315 - octoprint.plugins.announcements - INFO - Loaded channel _blog from https://octoprint.org/feeds/octoblog.xml in 1.5s
2020-04-08 17:02:15,039 - octoprint.plugins.announcements - INFO - Loaded channel _blog from https://octoprint.org/feeds/octoblog.xml in 1.2s
2020-04-08 17:02:15,661 - octoprint.plugins.announcements - INFO - Loaded channel _plugins from https://plugins.octoprint.org/feed.xml in 1.1s
2020-04-08 17:02:16,197 - octoprint.plugins.announcements - INFO - Loaded channel _plugins from https://plugins.octoprint.org/feed.xml in 0.94s
2020-04-08 17:02:17,117 - octoprint.plugins.announcements - INFO - Loaded channel _octopi from https://octoprint.org/feeds/octopi.xml in 1.1s
2020-04-08 17:02:17,468 - octoprint.plugins.announcements - INFO - Loaded channel _octopi from https://octoprint.org/feeds/octopi.xml in 0.92s
2020-04-08 17:02:24,196 - octoprint.util.pip - INFO - pip installs to /home/pi/oprint/lib/python2.7/site-packages/ (writable -> yes), --user flag needed -> no, virtual env -> yes
2020-04-08 17:02:24,197 - octoprint.util.pip - INFO - ==> pip ok -> yes
2020-04-08 17:02:24,205 - octoprint.util.pip - INFO - pip installs to /home/pi/oprint/lib/python2.7/site-packages (writable -> yes), --user flag needed -> no, virtual env -> yes
2020-04-08 17:02:24,209 - octoprint.util.pip - INFO - ==> pip ok -> yes
2020-04-08 17:02:24,365 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2020-04-08 17:02:24,369 - octoprint.plugins.stlviewer - INFO - STL Viewer loaded!
2020-04-08 17:02:24,377 - octoprint.plugin - ERROR - Error while calling plugin tracking
Traceback (most recent call last):
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/plugin/__init__.py", line 230, in call_plugin
    result = getattr(plugin, method)(*args, **kwargs)
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/tracking/__init__.py", line 101, in on_after_startup
    self._track_startup()
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/tracking/__init__.py", line 168, in _track_startup
    os=self._environment[b"os"][b"id"],
TypeError: 'NoneType' object has no attribute '__getitem__'
2020-04-08 17:02:29,033 - octoprint.plugins.tracking - INFO - Sent tracking event system_unthrottled, payload: {'throttled_mask': 327680, 'throttled_voltage_now': False, 'throttled_voltage_past': True, 'throttled_overheat_now': False, '
throttled_now': False, 'throttled_past': True, 'throttled_overheat_past': False}
2020-04-08 17:03:18,714 - tornado.access - WARNING - 404 GET /favicon.ico (192.168.86.36) 24.12ms
2020-04-08 17:03:18,743 - octoprint.server.util.sockjs - INFO - New connection from client: 192.168.86.36
2020-04-08 17:03:27,966 - octoprint.server.api - INFO - Actively logging in user aneta8 from 192.168.86.36
2020-04-08 17:03:28,093 - octoprint.server.util.sockjs - INFO - Client connection closed: 192.168.86.36
2020-04-08 17:03:28,359 - octoprint.server.util.sockjs - INFO - New connection from client: 192.168.86.36
2020-04-08 17:03:38,986 - tornado.access - WARNING - 401 POST /api/login (192.168.86.36) 32.00ms
2020-04-08 17:03:44,918 - octoprint.server.api - INFO - Actively logging in user aneta8 from 192.168.86.36
2020-04-08 17:03:45,115 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:03:45,128 - octoprint.server.util.flask.PreemptiveCache - INFO - Adding entry for / and {'query_string': 'l10n=en', 'path': u'/', '_count': 1, '_timestamp': 1586383425.128539, 'base_url': 'http://192.168.86.198/'}
2020-04-08 17:04:10,931 - octoprint.server.util.sockjs - INFO - Client connection closed: 192.168.86.36
2020-04-08 17:04:13,028 - octoprint.server.util.sockjs - INFO - New connection from client: 192.168.86.36
2020-04-08 17:04:13,211 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:04:18,497 - octoprint.server.util.sockjs - INFO - User aneta8 logged in on the socket from client 192.168.86.36
2020-04-08 17:05:48,621 - octoprint.plugins.softwareupdate - INFO - Starting update of octoprint to 1.4.0...
2020-04-08 17:06:13,784 - octoprint.plugins.softwareupdate - ERROR - Update of octoprint can not be performed, please also check plugin_softwareupdate_console.log for possible causes of this
Traceback (most recent call last):
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate/__init__.py", line 969, in _perform_update
    update_result = updater.perform_update(target, populated_check, target_version, log_cb=self._log, online=online)
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate/updaters/pip.py", line 116, in perform_update
    raise exceptions.UpdateError("Error while executing pip install", (stdout, stderr))
UpdateError
2020-04-08 17:06:14,684 - octoprint.plugins.tracking - INFO - Sent tracking event update_failed, payload: {'to_version': u'1.4.0', 'from_version': u'1.3.10', 'target': 'octoprint'}
2020-04-08 17:12:28,992 - octoprint.plugins.tracking - INFO - Sent tracking event system_throttled, payload: {'throttled_mask': 327685, 'throttled_voltage_now': True, 'throttled_voltage_past': True, 'throttled_overheat_now': False, 'thr
ottled_now': True, 'throttled_past': True, 'throttled_overheat_past': False}
2020-04-08 17:16:42,685 - octoprint.server.heartbeat - INFO - Server heartbeat <3
2020-04-08 17:17:25,673 - octoprint.plugins.tracking - INFO - Sent tracking event ping, payload: {}
2020-04-08 17:22:00,428 - octoprint.plugins.tracking - INFO - Sent tracking event system_unthrottled, payload: {'throttled_mask': 327680, 'throttled_voltage_now': False, 'throttled_voltage_past': True, 'throttled_overheat_now': False, '
throttled_now': False, 'throttled_past': True, 'throttled_overheat_past': False}
2020-04-08 17:23:28,374 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:23:28,540 - octoprint.server.util.sockjs - INFO - Client connection closed: 192.168.86.36
2020-04-08 17:23:29,203 - octoprint.server.util.sockjs - INFO - New connection from client: 192.168.86.36
2020-04-08 17:23:29,379 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:23:33,693 - octoprint.server.util.sockjs - INFO - User aneta8 logged in on the socket from client 192.168.86.36
2020-04-08 17:23:53,797 - octoprint.server.util.sockjs - INFO - Client connection closed: 192.168.86.36
2020-04-08 17:24:26,963 - octoprint.server.util.sockjs - INFO - New connection from client: 192.168.86.36
2020-04-08 17:24:27,246 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:24:30,747 - octoprint.server.util.sockjs - INFO - User aneta8 logged in on the socket from client 192.168.86.36
2020-04-08 17:24:36,259 - octoprint.plugins.softwareupdate - INFO - Starting update of octoprint to 1.4.0...
2020-04-08 17:25:01,643 - octoprint.plugins.softwareupdate - ERROR - Update of octoprint can not be performed, please also check plugin_softwareupdate_console.log for possible causes of this
Traceback (most recent call last):
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate/__init__.py", line 969, in _perform_update
    update_result = updater.perform_update(target, populated_check, target_version, log_cb=self._log, online=online)
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate/updaters/pip.py", line 116, in perform_update
    raise exceptions.UpdateError("Error while executing pip install", (stdout, stderr))
UpdateError
2020-04-08 17:25:02,541 - octoprint.plugins.tracking - INFO - Sent tracking event update_failed, payload: {'to_version': u'1.4.0', 'from_version': u'1.3.10', 'target': 'octoprint'}
2020-04-08 17:29:16,040 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:29:16,263 - octoprint.server.util.sockjs - INFO - Client connection closed: 192.168.86.36
2020-04-08 17:29:16,830 - octoprint.server.util.sockjs - INFO - New connection from client: 192.168.86.36
2020-04-08 17:29:17,014 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:29:20,614 - octoprint.server.util.sockjs - INFO - User aneta8 logged in on the socket from client 192.168.86.36
2020-04-08 17:29:28,151 - octoprint.plugins.softwareupdate - INFO - Starting update of octoprint to 1.4.0...
2020-04-08 17:29:52,651 - octoprint.plugins.softwareupdate - ERROR - Update of octoprint can not be performed, please also check plugin_softwareupdate_console.log for possible causes of this
Traceback (most recent call last):
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate/__init__.py", line 969, in _perform_update
    update_result = updater.perform_update(target, populated_check, target_version, log_cb=self._log, online=online)
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate/updaters/pip.py", line 116, in perform_update
    raise exceptions.UpdateError("Error while executing pip install", (stdout, stderr))
UpdateError
2020-04-08 17:29:53,524 - octoprint.plugins.tracking - INFO - Sent tracking event update_failed, payload: {'to_version': u'1.4.0', 'from_version': u'1.3.10', 'target': 'octoprint'}
2020-04-08 17:31:42,688 - octoprint.server.heartbeat - INFO - Server heartbeat <3
2020-04-08 17:32:06,302 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:32:06,454 - octoprint.server.util.sockjs - INFO - Client connection closed: 192.168.86.36
2020-04-08 17:32:07,061 - octoprint.server.util.sockjs - INFO - New connection from client: 192.168.86.36
2020-04-08 17:32:07,230 - octoprint.server.util.flask - INFO - Passively logging in user aneta8 from 192.168.86.36
2020-04-08 17:32:10,738 - octoprint.server.util.sockjs - INFO - User aneta8 logged in on the socket from client 192.168.86.36
2020-04-08 17:32:25,529 - octoprint.plugins.tracking - INFO - Sent tracking event ping, payload: {}

Read through this thread which appears to be the same situation.

Specifically this post with a temporary solution:

The actual solution is to update your setup.