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It appears that the ollama model list is hard-coded to just one model, which might-or-might-not actually be locally available.
I'll follow with a patch that detects an Ollama install and instead uses the actual list available, and has an empty list if none are availaable.
My example config demonstrates the problem. For this config, the first three expand as expected, and the 4th explicity ollama model works, but for the final entry it doesn't expand:
model_list:
  - model_name: perplexity/*
    litellm_params:
      model: perplexity/*
      api_key: os.environ/PERPLEXITY_API_KEY
  - model_name: anthropic/*
    litellm_params:
      model: anthropic/*
      api_key: os.environ/ANTHROPIC_API_KEY
  
  - model_name: openai/*
    litellm_params:
      model: openai/*
      api_key: os.environ/OPENAI_API_KEY
 
  - model_name: ollama_chat/deepseek-r1:14b
    litellm_params:
      model: ollama_chat/deepseek-r1:14b
      api_base: "http://localhost:11434"
  
  - model_name: ollama_chat/*
    litellm_params:
      model: ollama_chat/*
      api_base: "http://localhost:11434"
Full launch output with --detailed_debug:
> litellm --config litellm-config/litellm-config.yaml --detailed_debug
(venv-openwebui) ssmith@Scott-Laptop-2024 ~/open-webui (0.5.7-ss1)
> litellm --config litellm-config/litellm-config.yaml --detailed_debug
/Users/ssmith/open-webui/backend/venv-openwebui/lib/python3.11/site-packages/pydantic/_internal/_config.py:341: UserWarning: Valid config keys have changed in V2:
* 'fields' has been removed
  warnings.warn(message, UserWarning)
INFO:     Started server process [24689]
INFO:     Waiting for application startup.
10:35:37 - LiteLLM Proxy:DEBUG: proxy_server.py:442 - litellm.proxy.proxy_server.py::startup() - CHECKING PREMIUM USER - False
10:35:37 - LiteLLM Proxy:DEBUG: litellm_license.py:98 - litellm.proxy.auth.litellm_license.py::is_premium() - ENTERING 'IS_PREMIUM' - LiteLLM License=None
10:35:37 - LiteLLM Proxy:DEBUG: litellm_license.py:107 - litellm.proxy.auth.litellm_license.py::is_premium() - Updated 'self.license_str' - None
10:35:37 - LiteLLM Proxy:DEBUG: proxy_server.py:453 - worker_config: {"model": null, "alias": null, "api_base": null, "api_version": "2024-07-01-preview", "debug": false, "detailed_debug": true, "temperature": null, "max_tokens": null, "request_timeout": null, "max_budget": null, "telemetry": true, "drop_params": false, "add_function_to_prompt": false, "headers": null, "save": false, "config": "litellm-config/litellm-config.yaml", "use_queue": false}
#------------------------------------------------------------#
#                                                            #
#               'A feature I really want is...'               #
#        https://github.com/BerriAI/litellm/issues/new        #
#                                                            #
#------------------------------------------------------------#
 Thank you for using LiteLLM! - Krrish & Ishaan
Give Feedback / Get Help: https://github.com/BerriAI/litellm/issues/new
10:35:37 - LiteLLM Proxy:DEBUG: proxy_server.py:1500 - loaded config={
    "model_list": [
        {
            "model_name": "perplexity/*",
            "litellm_params": {
                "model": "perplexity/*",
                "api_key": "os.environ/PERPLEXITY_API_KEY"
            }
        },
        {
            "model_name": "anthropic/*",
            "litellm_params": {
                "model": "anthropic/*",
                "api_key": "os.environ/ANTHROPIC_API_KEY"
            }
        },
        {
            "model_name": "openai/*",
            "litellm_params": {
                "model": "openai/*",
                "api_key": "os.environ/OPENAI_API_KEY"
            }
        },
        {
            "model_name": "ollama_chat/deepseek-r1:14b",
            "litellm_params": {
                "model": "ollama_chat/deepseek-r1:14b",
                "api_base": "http://localhost:11434"
            }
        },
        {
            "model_name": "ollama_chat/*",
            "litellm_params": {
                "model": "ollama_chat/*",
                "api_base": "http://localhost:11434"
            }
        }
    ]
}
LiteLLM: Proxy initialized with Config, Set models:
    perplexity/*
    anthropic/*
    openai/*
    ollama_chat/deepseek-r1:14b
    ollama_chat/*
10:35:37 - LiteLLM:DEBUG: utils.py:4323 - Error getting model info: This model isn't mapped yet. Add it here - https://github.com/BerriAI/litellm/blob/main/model_prices_and_context_window.json
10:35:37 - LiteLLM Router:DEBUG: client_initalization_utils.py:468 - Initializing OpenAI Client for perplexity/*, Api Base:https://api.perplexity.ai, Api Key:pplx-5LC***************
10:35:37 - LiteLLM:DEBUG: utils.py:4323 - Error getting model info: This model isn't mapped yet. Add it here - https://github.com/BerriAI/litellm/blob/main/model_prices_and_context_window.json
10:35:37 - LiteLLM Router:DEBUG: client_initalization_utils.py:468 - Initializing OpenAI Client for openai/*, Api Base:None, Api Key:sk-proj-***************
10:35:37 - LiteLLM:DEBUG: utils.py:4323 - Error getting model info: OllamaError: Error getting model info for *. Set Ollama API Base via `OLLAMA_API_BASE` environment variable. Error: Server error '500 Internal Server Error' for url 'http://localhost:11434/api/show'
For more information check: https://developer.mozilla.org/en-US/docs/Web/HTTP/Status/500
10:35:37 - LiteLLM Router:DEBUG: router.py:4038 - 
Initialized Model List ['perplexity/*', 'anthropic/*', 'openai/*', 'ollama_chat/deepseek-r1:14b', 'ollama_chat/*']
10:35:37 - LiteLLM Router:INFO: router.py:613 - Routing strategy: simple-shuffle
10:35:37 - LiteLLM Router:DEBUG: router.py:505 - Intialized router with Routing strategy: simple-shuffle
Routing enable_pre_call_checks: False
Routing fallbacks: None
Routing content fallbacks: None
Routing context window fallbacks: None
Router Redis Caching=None
10:35:37 - LiteLLM Proxy:DEBUG: proxy_server.py:518 - prisma_client: None
INFO:     Application startup complete.
INFO:     Uvicorn running on http://0.0.0.0:4000 (Press CTRL+C to quit)
The key error seems to be:
10:35:37 - LiteLLM:DEBUG: utils.py:4323 - Error getting model info: OllamaError: Error getting model info for *. Set Ollama API Base via `OLLAMA_API_BASE` environment variable. Error: Server error '500 Internal Server Error' for url 'http://localhost:11434/api/show'
Note that the error about the env var was different at first, and I set that value:
export OLLAMA_API_BASE=http://localhost:11434
The error message is misleading b/c that URL does return correct model info, just not for "*".