diff --git a/handlers/sshd_config/analyzer/options.go b/handlers/sshd_config/analyzer/options.go
index 58132b3..13140f0 100644
--- a/handlers/sshd_config/analyzer/options.go
+++ b/handlers/sshd_config/analyzer/options.go
@@ -18,42 +18,100 @@ func analyzeOptionsAreValid(
 	it := d.Config.Options.Iterator()
 
 	for it.Next() {
-		line := it.Key().(uint32)
 		entry := it.Value().(ast.SSHEntry)
 
-		option := entry.GetOption()
-
-		if option.Key != nil {
-			docOption, found := fields.Options[option.Key.Value]
-
-			if !found {
-				errs = append(errs, common.LSPError{
-					Range: option.Key.LocationRange,
-					Err:   errors.New(fmt.Sprintf("Unknown option: %s", option.Key.Value)),
-				})
-				continue
-			}
-
-			if option.OptionValue == nil {
-				continue
-			}
-
-			invalidValues := docOption.CheckIsValid(option.OptionValue.Value)
-
-			errs = append(
-				errs,
-				utils.Map(
-					invalidValues,
-					func(invalidValue *docvalues.InvalidValue) common.LSPError {
-						err := docvalues.LSPErrorFromInvalidValue(line, *invalidValue)
-						err.ShiftCharacter(option.OptionValue.Start.Character)
-
-						return err
-					},
-				)...,
-			)
-
+		switch entry.(type) {
+		case *ast.SSHOption:
+			errs = append(errs, checkOption(entry.(*ast.SSHOption), false)...)
+		case *ast.SSHMatchBlock:
+			matchBlock := entry.(*ast.SSHMatchBlock)
+			errs = append(errs, checkMatchBlock(matchBlock)...)
 		}
+
+	}
+
+	return errs
+}
+
+func checkOption(
+	option *ast.SSHOption,
+	isInMatchBlock bool,
+) []common.LSPError {
+	errs := make([]common.LSPError, 0)
+
+	if option.Key != nil {
+		docOption, found := fields.Options[option.Key.Value]
+
+		if !found {
+			errs = append(errs, common.LSPError{
+				Range: option.Key.LocationRange,
+				Err:   errors.New(fmt.Sprintf("Unknown option: %s", option.Key.Value)),
+			})
+
+			return errs
+		}
+
+		if _, found := fields.MatchAllowedOptions[option.Key.Value]; !found && isInMatchBlock {
+			errs = append(errs, common.LSPError{
+				Range: option.Key.LocationRange,
+				Err:   errors.New(fmt.Sprintf("Option '%s' is not allowed inside Match blocks", option.Key.Value)),
+			})
+
+			return errs
+		}
+
+		if option.OptionValue == nil {
+			return errs
+		}
+
+		invalidValues := docOption.CheckIsValid(option.OptionValue.Value)
+
+		errs = append(
+			errs,
+			utils.Map(
+				invalidValues,
+				func(invalidValue *docvalues.InvalidValue) common.LSPError {
+					err := docvalues.LSPErrorFromInvalidValue(option.Start.Line, *invalidValue)
+					err.ShiftCharacter(option.OptionValue.Start.Character)
+
+					return err
+				},
+			)...,
+		)
+	}
+
+	return errs
+}
+
+func checkMatchBlock(
+	matchBlock *ast.SSHMatchBlock,
+) []common.LSPError {
+	errs := make([]common.LSPError, 0)
+
+	matchOption := matchBlock.MatchEntry.OptionValue
+	if matchOption != nil {
+		invalidValues := fields.Options["Match"].CheckIsValid(matchOption.Value)
+
+		errs = append(
+			errs,
+			utils.Map(
+				invalidValues,
+				func(invalidValue *docvalues.InvalidValue) common.LSPError {
+					err := docvalues.LSPErrorFromInvalidValue(matchBlock.Start.Line, *invalidValue)
+					err.ShiftCharacter(matchOption.Start.Character)
+
+					return err
+				},
+			)...,
+		)
+	}
+
+	it := matchBlock.Options.Iterator()
+
+	for it.Next() {
+		option := it.Value().(*ast.SSHOption)
+
+		errs = append(errs, checkOption(option, true)...)
 	}
 
 	return errs
diff --git a/handlers/sshd_config/fields/fields.go b/handlers/sshd_config/fields/fields.go
index 4de4c20..41a233c 100644
--- a/handlers/sshd_config/fields/fields.go
+++ b/handlers/sshd_config/fields/fields.go
@@ -574,8 +574,8 @@ Only a subset of keywords may be used on the lines following a Match keyword. Av
 					SubValue: docvalues.KeyEnumAssignmentValue{
 						Separator: " ",
 						Values: map[docvalues.EnumString]docvalues.Value{
-							docvalues.CreateEnumString("User"):         docvalues.UserValue("", true),
-							docvalues.CreateEnumString("Group"):        docvalues.GroupValue("", true),
+							docvalues.CreateEnumString("User"):         docvalues.StringValue{},
+							docvalues.CreateEnumString("Group"):        docvalues.StringValue{},
 							docvalues.CreateEnumString("Host"):         docvalues.StringValue{},
 							docvalues.CreateEnumString("LocalAddress"): docvalues.StringValue{},
 							docvalues.CreateEnumString("LocalPort"):    docvalues.NumberValue{Min: &ZERO, Max: &MAX_PORT},
diff --git a/handlers/sshd_config/lsp/text-document-hover.go b/handlers/sshd_config/lsp/text-document-hover.go
index 61d19cd..bb73a41 100644
--- a/handlers/sshd_config/lsp/text-document-hover.go
+++ b/handlers/sshd_config/lsp/text-document-hover.go
@@ -9,5 +9,12 @@ func TextDocumentHover(
 	context *glsp.Context,
 	params *protocol.HoverParams,
 ) (*protocol.Hover, error) {
+	// line := params.Position.Line
+	// cursor := params.Position.Character
+	//
+	// d := sshdconfig.DocumentParserMap[params.TextDocument.URI]
+	//
+	// entry, matchBlock := d.Config.FindOption(line)
+
 	return nil, nil
 }