[Bug]: 500 Internal Server Error Server got itself in trouble

[38Cherry]

Describe the bug

AMP stopped working for me and have tried everything. No matter what when trying to authorize AMP after the Amazon log in screen i get
http://192.168.1.236:8123/auth/alexamedia/proxy/verify
500 Internal Server Error
Server got itself in trouble

I've tried deleted everything down to the pickle files and downloading but i can't get past the 500. Not sure where to find any logs that may help. At first i thought maybe an alexa+ issue but i downgraded (upgraded????) back to regular alexa and no change. Stumped. Running HASS OS on proxmox.

I also tried rolling back to my old vbox vdi and it give the same result and it was working when i shut it down a couple weeks ago.

To Reproduce

try to install

Expected behavior

install and authorize

Screenshots

No response

Home Assistant Version

2026.1.2

Alexa Media Player Version

5.10.0

Alexa Media Player API library Version

?

Have you entered a 52-character key for Amazon 2SV via Authenticator App login?

YES

Is the HA core integration Alexa Devices installed?

Trying

Amazon Domain

amazon.com (US)

Amazon Domain (if Other)

No response

Debug Logs (alexa_media & alexapy)

Additional context

No response

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⚠️ Possible Duplicate Issue

• Still unable to login, even after updating to 5.7.11 #3104

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[Michael-Robson]

Same issue I'm running HA on DietPi.
HA:
Core: 2025.12.5
Frontend: 20251203.3

Alexa Media Player: V5.10.0

[danielbrunt57]

Enable debug logs for alexa_media and alexapy & restart Home Assistant.

logger:
  default: info
  logs:
    alexapy: debug
    custom_components.alexa_media: debug

View debug logs:
Settings > System > Logs > 3-dot menu upper right > Show raw logs > Search logs: alexa

[danielbrunt57]

Make sure the logs include the beginning of AMP configuration..

[38Cherry]

rolled back to an old snap shot and AMP was working. Started the update process and updating HA Supervisor to 26.1

2026.01.1 broke AMP (asking to reauth but that may just be because of all the deleted authenticator apps from this process)

2026-01-20 16:26:14.963 DEBUG (MainThread) [custom_components.alexa_media.config_flow] Using existing login
2026-01-20 16:26:14.963 DEBUG (MainThread) [alexapy.alexalogin] Creating TOTP with authenticator app key L************************67A
2026-01-20 16:26:14.963 DEBUG (MainThread) [alexapy.alexalogin] Generated OTP: 8141
2026-01-20 16:26:14.995 DEBUG (MainThread) [alexapy.alexalogin] Generated OTP: 8141
2026-01-20 16:26:14.995 DEBUG (MainThread) [custom_components.alexa_media.config_flow] Generated TOTP: 815441
2026-01-20 16:26:28.746 DEBUG (MainThread) [custom_components.alexa_media.config_flow] Starting proxy for a1@gm - amazon.com
2026-01-20 16:26:28.747 DEBUG (MainThread) [alexapy.alexalogin] Attempting oauth login to https://www.amazon.com/ap/register?openid.return_to=https://www.amazon.com/ap/maplanding&openid.assoc_handle=amzn_dp_project_dee_ios&openid.identity=http://specs.openid.net/auth/2.0/identifier_select&pageId=amzn_dp_project_dee_ios&accountStatusPolicy=P1&openid.claimed_id=http://specs.openid.net/auth/2.0/identifier_select&openid.mode=checkid_setup&openid.ns.oa2=http://www.amazon.com/ap/ext/oauth/2&openid.oa2.client_id=device:323361653665653339373334323933376137616661386133323939323832633532333431333234393536346335363335353634643332353733383331&openid.ns.pape=http://specs.openid.net/extensions/pape/1.0&openid.oa2.response_type=code&openid.ns=http://specs.openid.net/auth/2.0&openid.pape.max_auth_age=0&openid.oa2.scope=device_auth_access+offline_access&openid.oa2.code_challenge_method=S256&openid.oa2.code_challenge=eCvXBP34UVNmTizIVTc54R_mkVexajxFs_blcrzP-NU&language=en_US
2026-01-20 16:26:28.748 DEBUG (MainThread) [alexapy.alexalogin] Generated OTP: 8141
2026-01-20 16:26:28.748 DEBUG (MainThread) [alexapy.alexalogin] Generated OTP: 8141
2026-01-20 16:26:28.785 DEBUG (MainThread) [custom_components.alexa_media.config_flow] Found flow_id; adding 192.168.1.65 to known_ips for 300 seconds
File "/config/custom_components/alexa_media/config_flow.py", line 1067, in wrapped

[danielbrunt57]

@38Cherry Did you reboot your HA hardware after the supervisor update?

[Patneys]

Facing same issue
"500 Internal Server Error
Server got itself in trouble"

HAOS updated versions

[Spettacolo83]

Same issue here. Tried multiple troubleshooting steps without success.

Environment

• Installation method: Home Assistant OS
• Core: 2026.1.2
• Supervisor: 2026.01.1
• Operating System: 17.0
• Frontend: 20260107.2
• Alexa Media Player: 5.10.0 (also tried 5.8.4)
• Amazon domain: amazon.it
• 2FA: Disabled

Error

500 Internal Server Error - Server got itself in trouble

Occurs at /auth/alexamedia/proxy/verify after completing Amazon login.

Troubleshooting attempted (all failed):

1. ✗ Cleared browser cache and cookies
2. ✗ Tried different browsers (Chrome, Firefox, Safari)
3. ✗ Used incognito/private browsing window
4. ✗ Accessed HA via local IP only (http://192.168.1.103:8123)
5. ✗ Changed password directly in core.config_entries file
6. ✗ Cleared OAuth tokens from core.config_entries (set "oauth":{})
7. ✗ Downgraded Alexa Media Player from 5.10.0 to 5.8.4
8. ✗ Full hardware reboot (power cycle Raspberry Pi 5)
9. ✗ Completely removed and reinstalled the integration from HACS

None of the above resolved the issue. The 500 error persists regardless of version or configuration
changes.

This seems to be related to Supervisor 2026.01.1 as mentioned by other users.

[danielbrunt57]

• 2FA: Disabled

Installation and Configuration (wiki)

Enable Two-Step Verification for your Amazon account

Your preferred method must be via Authenticator App.
No help will be provided for any authentication issues if you attempt to configure otherwise.

[nineknives]

I am running into this issue as well. I have 2FA enabled and followed all steps using the 52 character code in lieu of the barcode scan. The integration setup works until it provides the OTP to give back to Amazon. After that step it redirects to an Amazon log in page. After confirming sign-in it redirects to a 500 error page. To my knowledge I am following the documentation install instructions to a T. This previously worked in my build but since the 2026.01 release has not worked.

[danielbrunt57]

Is authenticator app the preferred method?

[danielbrunt57]

It's possible that Amazon is trying to present a page that alexapy.alexalogin/alexa_media.config_flow as never programmed for.
I'm not sure if the relevant portions of code have any meaningful debug messages or not.
Without debug messages to unravel, it's like a black box that works well but only when the stars align. If not, ¯\_(ツ)_/¯

I think I recall reading that some users fixed it by deleting 2SV, changing Amazon account password and setting up 2SV again.