diff --git a/BirthdayBot/BackgroundServices/BirthdayRoleUpdate.vb b/BirthdayBot/BackgroundServices/BirthdayRoleUpdate.vb
index 3afcd45..fac7736 100644
--- a/BirthdayBot/BackgroundServices/BirthdayRoleUpdate.vb
+++ b/BirthdayBot/BackgroundServices/BirthdayRoleUpdate.vb
@@ -69,10 +69,11 @@ Class BirthdayRoleUpdate
             If gs.AnnounceChannelId.HasValue Then channel = guild.GetTextChannel(gs.AnnounceChannelId.Value)
             If gs.RoleId.HasValue Then role = guild.GetRole(gs.RoleId.Value)
             If role Is Nothing Then
-                gs.RoleWarning = True
+                gs.RoleWarningNonexist = True
                 Return 0
+            Else
+                gs.RoleWarningNonexist = False
             End If
-            gs.RoleWarning = False
         End SyncLock
 
         ' Determine who's currently having a birthday
@@ -81,28 +82,29 @@ Class BirthdayRoleUpdate
 
         ' Set birthday roles, get list of users that had the role added
         ' But first check if we are able to do so. Letting all requests fail instead will lead to rate limiting.
-        Dim announceNames As IEnumerable(Of SocketGuildUser)
-        If HasCorrectRolePermissions(guild, role) Then
+        Dim correctRolePermissions = HasCorrectRolePermissions(guild, role)
+        Dim gotForbidden = False
+
+        Dim announceNames As IEnumerable(Of SocketGuildUser) = Nothing
+        If correctRolePermissions Then
             Try
                 announceNames = Await UpdateGuildBirthdayRoles(guild, role, birthdays)
             Catch ex As Discord.Net.HttpException
                 If ex.HttpCode = HttpStatusCode.Forbidden Then
-                    announceNames = Nothing
+                    gotForbidden = True
                 Else
                     Throw
                 End If
             End Try
-        Else
-            announceNames = Nothing
         End If
 
-        If announceNames Is Nothing Then
-            SyncLock BotInstance.KnownGuilds
-                ' Nothing on announceNAmes signals failure to apply roles. Set the warning message.
-                BotInstance.KnownGuilds(guild.Id).RoleWarning = True
-            End SyncLock
-            Return 0
-        End If
+        ' Update warning flag
+        Dim updateError = Not correctRolePermissions Or gotForbidden
+        SyncLock BotInstance.KnownGuilds
+            BotInstance.KnownGuilds(guild.Id).RoleWarningPermission = updateError
+        End SyncLock
+        ' Quit now if the warning flag was set. Announcement data is not available.
+        If updateError Then Return 0
 
         If announceNames.Count <> 0 Then
             ' Send out announcement message
diff --git a/BirthdayBot/BirthdayBot.vb b/BirthdayBot/BirthdayBot.vb
index a6a45aa..47685bd 100644
--- a/BirthdayBot/BirthdayBot.vb
+++ b/BirthdayBot/BirthdayBot.vb
@@ -26,12 +26,12 @@ Class BirthdayBot
     End Property
 
     ''' <summary>SyncLock when using. The lock object is itself.</summary>
-    Friend ReadOnly Property KnownGuilds As Dictionary(Of ULong, GuildSettings)
+    Friend ReadOnly Property KnownGuilds As Dictionary(Of ULong, GuildStateInformation)
 
     Public Sub New(conf As Configuration, dc As DiscordSocketClient)
         Config = conf
         _client = dc
-        KnownGuilds = New Dictionary(Of ULong, GuildSettings)
+        KnownGuilds = New Dictionary(Of ULong, GuildStateInformation)
 
         _worker = New BackgroundServiceRunner(Me)
 
@@ -75,7 +75,7 @@ Class BirthdayBot
     Private Function LoadGuild(g As SocketGuild) As Task Handles _client.JoinedGuild, _client.GuildAvailable
         SyncLock KnownGuilds
             If Not KnownGuilds.ContainsKey(g.Id) Then
-                Dim gi = GuildSettings.LoadSettingsAsync(Config.DatabaseSettings, g.Id).GetAwaiter().GetResult()
+                Dim gi = GuildStateInformation.LoadSettingsAsync(Config.DatabaseSettings, g.Id).GetAwaiter().GetResult()
                 KnownGuilds.Add(g.Id, gi)
             End If
         End SyncLock
@@ -114,7 +114,7 @@ Class BirthdayBot
                 End If
 
                 ' Ban and role warning check
-                Dim roleWarning As Boolean
+                Dim roleWarningText As String
                 SyncLock KnownGuilds
                     Dim gi = KnownGuilds(channel.Guild.Id)
 
@@ -125,13 +125,13 @@ Class BirthdayBot
                         End If
                     End If
 
-                    roleWarning = gi.RoleWarning
+                    roleWarningText = gi.IssueRoleWarning
                 End SyncLock
 
                 Try
-                    If roleWarning Then
+                    If roleWarningText IsNot Nothing Then
                         Try
-                            Await channel.SendMessageAsync(RoleWarningMsg)
+                            Await channel.SendMessageAsync(roleWarningText)
                         Catch ex As HttpException
                             ' Don't let this prevent the bot from continuing command execution.
                         End Try
diff --git a/BirthdayBot/Data/Database.vb b/BirthdayBot/Data/Database.vb
index 1300e47..17c4a90 100644
--- a/BirthdayBot/Data/Database.vb
+++ b/BirthdayBot/Data/Database.vb
@@ -26,7 +26,7 @@ Class Database
 
     Private Sub SetupTables()
         Using db = OpenConnectionAsync().GetAwaiter().GetResult()
-            GuildSettings.SetUpDatabaseTable(db) ' Note: Call this first. (Foreign reference constraints.)
+            GuildStateInformation.SetUpDatabaseTable(db) ' Note: Call this first. (Foreign reference constraints.)
             GuildUserSettings.SetUpDatabaseTable(db)
         End Using
     End Sub
diff --git a/BirthdayBot/Data/GuildSettings.vb b/BirthdayBot/Data/GuildStateInformation.vb
similarity index 86%
rename from BirthdayBot/Data/GuildSettings.vb
rename to BirthdayBot/Data/GuildStateInformation.vb
index 7dccbef..0eeeb6a 100644
--- a/BirthdayBot/Data/GuildSettings.vb
+++ b/BirthdayBot/Data/GuildStateInformation.vb
@@ -4,11 +4,10 @@ Imports Npgsql
 Imports NpgsqlTypes
 
 ''' <summary>
-''' Collection of GuildUserSettings instances. Holds cached information on guild users and overall
-''' guild options, and provides some database abstractions regarding them all.
-''' Object instances are loaded when entering a guild and discarded when the bot leaves the guild.
+''' Holds various pieces of state information for a guild the bot is operating in.
+''' Includes, among other things, a copy of the guild's settings and a list of all known users with birthdays.
 ''' </summary>
-Friend Class GuildSettings
+Friend Class GuildStateInformation
     Public ReadOnly Property GuildId As ULong
     Private ReadOnly _db As Database
     Private _bdayRole As ULong?
@@ -19,33 +18,55 @@ Friend Class GuildSettings
     Private _announceMsg As String
     Private _announceMsgPl As String
     Private _announcePing As Boolean
-    Private _userCache As Dictionary(Of ULong, GuildUserSettings)
+    Private ReadOnly _userCache As Dictionary(Of ULong, GuildUserSettings)
 
-    Private _roleWarning As Boolean
     Private _roleLastWarning As New DateTimeOffset(DateTime.MinValue, TimeSpan.Zero)
     Private Shared ReadOnly RoleWarningInterval As New TimeSpan(1, 0, 0)
 
     ''' <summary>
-    ''' Flag for notifying servers that the bot is unable to manipulate its role.
-    ''' Can be set at any time. Reading this will only return True if it's been set as such,
-    ''' and it is only returned after a set time has passed in order to not constantly show the message.
+    ''' Message for notifying servers that the bot is unable to manipulate its designated role for various reasons.
+    ''' The returned value is dependent on certain warning flags accessible in this class. To avoid bombarding users
+    ''' with the same message, this property only returns a non-Nothing value at most once per hour.
+    ''' Otherwise, it shall always return Nothing if there is no warning to be issued.
     ''' </summary>
-    Public Property RoleWarning As Boolean
+    Public ReadOnly Property IssueRoleWarning As String
         Get
-            If _roleWarning = True Then
-                ' Only report a warning every so often.
-                If DateTimeOffset.UtcNow - _roleLastWarning > RoleWarningInterval Then
-                    _roleLastWarning = DateTimeOffset.UtcNow
-                    Return True
-                Else
-                    Return False
-                End If
+            If DateTimeOffset.UtcNow - _roleLastWarning > RoleWarningInterval Then
+                _roleLastWarning = DateTimeOffset.UtcNow
+            Else
+                Return Nothing
             End If
-            Return False
+
+            If RoleWarningUnset Or RoleWarningNonexist Then
+                Return "Warning: A birthday role must be configured before this bot can function properly. " +
+                    "Update the designated role with `bb.config role (role name/ID)`."
+            End If
+            If RoleWarningPermission Then
+                Return "Warning: This bot is unable to set the birthday role onto users. " +
+                    "Make sure that this bot has the Manage Roles permission and is not placed below the birthday role."
+            End If
+
+            Return Nothing
+        End Get
+    End Property
+
+    ''' <summary>
+    ''' Role warning message: The birthday role cannot be accessed.
+    ''' </summary>
+    Friend Property RoleWarningPermission As Boolean = False
+
+    ''' <summary>
+    ''' Role warning message: The birthday role no longer exists.
+    ''' </summary>
+    Friend Property RoleWarningNonexist As Boolean = False
+
+    ''' <summary>
+    ''' Role warning message: The birthday role is not set.
+    ''' </summary>
+    Friend ReadOnly Property RoleWarningUnset As Boolean
+        Get
+            Return _bdayRole Is Nothing
         End Get
-        Set(value As Boolean)
-            _roleWarning = value
-        End Set
     End Property
 
     ''' <summary>
@@ -132,9 +153,6 @@ Friend Class GuildSettings
         ' Weird: if using a ternary operator with a ULong?, Nothing resolves to 0 despite Option Strict On.
         If Not reader.IsDBNull(1) Then
             _bdayRole = CULng(reader.GetInt64(1))
-            RoleWarning = False
-        Else
-            RoleWarning = True
         End If
         If Not reader.IsDBNull(2) Then _announceCh = CULng(reader.GetInt64(2))
         _tz = If(reader.IsDBNull(3), Nothing, reader.GetString(3))
@@ -253,7 +271,6 @@ Friend Class GuildSettings
 
     Public Async Function UpdateRoleAsync(roleId As ULong) As Task
         _bdayRole = roleId
-        _roleWarning = False
         _roleLastWarning = New DateTimeOffset
         Await UpdateDatabaseAsync()
     End Function
@@ -326,7 +343,7 @@ Friend Class GuildSettings
     ''' Retrieves an object instance representative of guild settings for the specified guild.
     ''' If settings for the given guild do not yet exist, a new value is created.
     ''' </summary>
-    Friend Shared Async Function LoadSettingsAsync(dbsettings As Database, guild As ULong) As Task(Of GuildSettings)
+    Friend Shared Async Function LoadSettingsAsync(dbsettings As Database, guild As ULong) As Task(Of GuildStateInformation)
         Using db = Await dbsettings.OpenConnectionAsync()
             Using c = db.CreateCommand()
                 ' Take note of ordinals for use in the constructor
@@ -336,7 +353,7 @@ Friend Class GuildSettings
                 c.Prepare()
                 Using r = Await c.ExecuteReaderAsync()
                     If Await r.ReadAsync() Then
-                        Return New GuildSettings(r, dbsettings)
+                        Return New GuildStateInformation(r, dbsettings)
                     End If
                 End Using
             End Using
diff --git a/BirthdayBot/Data/GuildUserSettings.vb b/BirthdayBot/Data/GuildUserSettings.vb
index 257f1d0..d86d573 100644
--- a/BirthdayBot/Data/GuildUserSettings.vb
+++ b/BirthdayBot/Data/GuildUserSettings.vb
@@ -4,7 +4,7 @@ Imports NpgsqlTypes
 
 ''' <summary>
 ''' Representation of a user's birthday settings within a guild.
-''' Instances are held and managed by <see cref="GuildSettings"/>.
+''' Instances are held and managed by <see cref="GuildStateInformation"/>.
 ''' </summary>
 Class GuildUserSettings
     Private _month As Integer
@@ -125,7 +125,7 @@ Class GuildUserSettings
     Friend Shared Sub SetUpDatabaseTable(db As NpgsqlConnection)
         Using c = db.CreateCommand()
             c.CommandText = $"create table if not exists {BackingTable} (" +
-                $"guild_id bigint not null references {GuildSettings.BackingTable}, " +
+                $"guild_id bigint not null references {GuildStateInformation.BackingTable}, " +
                 "user_id bigint not null, " +
                 "birth_month integer not null, " +
                 "birth_day integer not null, " +