diff --git a/src/events/messageCreate.ts b/src/events/messageCreate.ts
index ae2341c..1ca7043 100644
--- a/src/events/messageCreate.ts
+++ b/src/events/messageCreate.ts
@@ -154,9 +154,9 @@ export default event(Events.MessageCreate, async ({ log, msgHist, ollama, client
                         if (config === undefined) {
                             redis.set(`server:${message.guildId}:config`, JSON.stringify({ options: { 'toggle-chat': true } }))
                                 .catch(err => log(`Failed to set default server config in Redis: ${err}`));
-                            reject(new Error('Failed to locate or create Server Preferences'))
+                            reject(new Error('Failed to locate or create Server Preferences\n\nPlease try chatting again...'))
                         } else if (!config.options['toggle-chat']) {
-                            reject(new Error('Admin(s) have disabled chat features'))
+                            reject(new Error('Admin(s) have disabled chat features.\n\nPlease contact your server\'s admin(s).'))
                         } else {
                             resolve(config)
                         }
@@ -166,10 +166,10 @@ export default event(Events.MessageCreate, async ({ log, msgHist, ollama, client
             } catch (error) {
                 ++attempt
                 if (attempt < maxRetries) {
-                    log(`Attempt ${attempt} failed for Server Preferences: ${error.message}. Retrying in ${delay}ms...`)
+                    log(`Attempt ${attempt} failed for Server Preferences. Retrying in ${delay}ms...`)
                     await new Promise(ret => setTimeout(ret, delay))
                 } else {
-                    log(`Could not retrieve Server Preferences after ${maxRetries} attempts: ${error.message}`)
+                    log(`Could not retrieve Server Preferences after ${maxRetries} attempts`)
                     message.reply(getFriendlyError())
                     return
                 }
@@ -206,7 +206,7 @@ export default event(Events.MessageCreate, async ({ log, msgHist, ollama, client
                             redis.set(userConfigKey, JSON.stringify(defaultConfig))
                                 .catch(err => log(`Failed to set default user config in Redis: ${err}`));
                             log(`Created default config for ${message.author.username}`)
-                            reject(new Error('No User Preferences set up. Created defaults.'))
+                            reject(new Error('No User Preferences is set up.\n\nCreating preferences with defaults.\nPlease try chatting again.'))
                             return
                         }
 
@@ -221,7 +221,7 @@ export default event(Events.MessageCreate, async ({ log, msgHist, ollama, client
                         shouldStream = config.options['message-stream'] || false
 
                         if (typeof config.options['switch-model'] !== 'string') {
-                            reject(new Error('No Model set. User must run `/switch-model` or `/pull-model`.'))
+                            reject(new Error(`No Model was set. Please set a model by running \`/switch-model <model of choice>\`.\n\nIf you do not have any models. Run \`/pull-model <model name>\`.`))
                         }
 
                         resolve(config)
@@ -234,10 +234,10 @@ export default event(Events.MessageCreate, async ({ log, msgHist, ollama, client
             } catch (error) {
                 ++attempt
                 if (attempt < maxRetries) {
-                    log(`Attempt ${attempt} failed for User Preferences: ${error.message}. Retrying in ${delay}ms...`)
+                    log(`Attempt ${attempt} failed for User Preferences. Retrying in ${delay}ms...`)
                     await new Promise(ret => setTimeout(ret, delay))
                 } else {
-                    log(`Could not retrieve User Preferences after ${maxRetries} attempts: ${error.message}`)
+                    log(`Could not retrieve User Preferences after ${maxRetries} attempts`)
                     message.reply(getFriendlyError())
                     return
                 }
@@ -267,7 +267,7 @@ export default event(Events.MessageCreate, async ({ log, msgHist, ollama, client
         }
 
         if (!userConfig) {
-            log(`Failed to initialize User Preference for ${message.author.username}: No config available`)
+            log(`Failed to initialize User Preference for **${message.author.username}**. No config available.`)
             message.reply(getFriendlyError())
             return
         }