diff --git a/core/cli/run.go b/core/cli/run.go
index 7583d97f9a81..015e2ce1d2c0 100644
--- a/core/cli/run.go
+++ b/core/cli/run.go
@@ -378,7 +378,7 @@ func (r *RunCMD) Run(ctx *cliContext.Context) error {
 
 	app, err := application.New(opts...)
 	if err != nil {
-		return fmt.Errorf("failed basic startup tasks with error %s", err.Error())
+		return fmt.Errorf("LocalAI failed to start: %w.\nTroubleshooting steps:\n  1. Check that your models directory exists and is accessible: %s\n  2. Verify model config files are valid YAML: 'local-ai util usecase-heuristic <config>'\n  3. Check available disk space and file permissions\n  4. Run with --log-level=debug for more details\nSee https://localai.io/basics/troubleshooting/ for more help", err, r.ModelsPath)
 	}
 
 	appHTTP, err := http.API(app)
diff --git a/core/cli/transcript.go b/core/cli/transcript.go
index 8da3892a0b39..341386540383 100644
--- a/core/cli/transcript.go
+++ b/core/cli/transcript.go
@@ -3,7 +3,6 @@ package cli
 import (
 	"context"
 	"encoding/json"
-	"errors"
 	"fmt"
 	"strings"
 
@@ -61,7 +60,7 @@ func (t *TranscriptCMD) Run(ctx *cliContext.Context) error {
 
 	c, exists := cl.GetModelConfig(t.Model)
 	if !exists {
-		return errors.New("model not found")
+		return fmt.Errorf("model %q not found. Run 'local-ai models list' to see available models, or install one with 'local-ai models install <model>'. See https://localai.io/models/ for more information", t.Model)
 	}
 
 	c.Threads = &t.Threads
diff --git a/core/cli/util.go b/core/cli/util.go
index b002e254e789..14ab9b561cdc 100644
--- a/core/cli/util.go
+++ b/core/cli/util.go
@@ -74,7 +74,7 @@ func (u *CreateOCIImageCMD) Run(ctx *cliContext.Context) error {
 
 func (u *GGUFInfoCMD) Run(ctx *cliContext.Context) error {
 	if len(u.Args) == 0 {
-		return fmt.Errorf("no GGUF file provided")
+		return fmt.Errorf("no GGUF file provided. Usage: local-ai util gguf-info <path-to-file.gguf>\nGGUF is a binary format for storing quantized language models. You can download GGUF models from https://huggingface.co or install one with 'local-ai models install <model>'")
 	}
 	// We try to guess only if we don't have a template defined already
 	f, err := gguf.ParseGGUFFile(u.Args[0])
diff --git a/core/cli/worker/worker_p2p.go b/core/cli/worker/worker_p2p.go
index 868357ccffd5..b843c44d972b 100644
--- a/core/cli/worker/worker_p2p.go
+++ b/core/cli/worker/worker_p2p.go
@@ -38,7 +38,7 @@ func (r *P2P) Run(ctx *cliContext.Context) error {
 	// Check if the token is set
 	// as we always need it.
 	if r.Token == "" {
-		return fmt.Errorf("Token is required")
+		return fmt.Errorf("a P2P token is required to join the network. Set it via the LOCALAI_TOKEN environment variable or the --token flag. You can generate a token by running 'local-ai run --p2p' on the main node. See https://localai.io/features/distribute/ for more information")
 	}
 
 	port, err := freeport.GetFreePort()
diff --git a/core/config/model_config_loader.go b/core/config/model_config_loader.go
index 68647a0867f6..7c214b186978 100644
--- a/core/config/model_config_loader.go
+++ b/core/config/model_config_loader.go
@@ -192,9 +192,9 @@ func (bcl *ModelConfigLoader) ReadModelConfig(file string, opts ...ConfigLoaderO
 		bcl.configs[c.Name] = *c
 	} else {
 		if err != nil {
-			return fmt.Errorf("config is not valid: %w", err)
+			return fmt.Errorf("model config %q is not valid: %w. Ensure the YAML file has a valid 'name' field and correct syntax. See https://localai.io/docs/getting-started/customize-model/ for config reference", file, err)
 		}
-		return fmt.Errorf("config is not valid")
+		return fmt.Errorf("model config %q is not valid. Ensure the YAML file has a valid 'name' field and correct syntax. See https://localai.io/docs/getting-started/customize-model/ for config reference", file)
 	}
 
 	return nil