diff --git a/extensions/typescript/test/colorize-fixtures/test-issue5566.ts b/extensions/typescript/test/colorize-fixtures/test-issue5566.ts
new file mode 100644
index 00000000000..55810e6783a
--- /dev/null
+++ b/extensions/typescript/test/colorize-fixtures/test-issue5566.ts
@@ -0,0 +1,3 @@
+function foo3() {
+	const foo = (): any => ({ 'bar': 'baz' })
+}
\ No newline at end of file
diff --git a/extensions/typescript/test/colorize-results/test-issue5566_ts.json b/extensions/typescript/test/colorize-results/test-issue5566_ts.json
new file mode 100644
index 00000000000..2933b403cd9
--- /dev/null
+++ b/extensions/typescript/test/colorize-results/test-issue5566_ts.json
@@ -0,0 +1,288 @@
+[
+	{
+		"c": "function",
+		"t": "function.meta.storage.ts.type",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.storage.type rgb(86, 156, 214)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.storage.type rgb(0, 0, 255)",
+			"dark_vs": ".vs-dark.vscode-theme-defaults-themes-dark_vs-json .token.storage.type rgb(86, 156, 214)",
+			"light_vs": ".vs.vscode-theme-defaults-themes-light_vs-json .token.storage.type rgb(0, 0, 255)",
+			"hc_black": ".hc-black.vscode-theme-defaults-themes-hc_black-json .token.storage.type rgb(86, 156, 214)"
+		}
+	},
+	{
+		"c": " ",
+		"t": "function.meta.ts",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "foo3",
+		"t": "entity.function.meta.name.ts",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.entity.name.function rgb(220, 220, 170)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.entity.name.function rgb(121, 94, 38)",
+			"dark_vs": ".vs-dark.vscode-theme-defaults-themes-dark_vs-json .token.entity.name.function rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "()",
+		"t": "brace.function.meta.parameter.round.ts.type",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": " ",
+		"t": "function.meta.ts",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "{",
+		"t": "block.brace.curly.decl.function.meta.ts",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "\t",
+		"t": "block.decl.expr.function.meta.ts.var",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "const",
+		"t": "block.decl.expr.function.meta.storage.ts.type.var",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.storage.type rgb(86, 156, 214)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.storage.type rgb(0, 0, 255)",
+			"dark_vs": ".vs-dark.vscode-theme-defaults-themes-dark_vs-json .token.storage.type rgb(86, 156, 214)",
+			"light_vs": ".vs.vscode-theme-defaults-themes-light_vs-json .token.storage.type rgb(0, 0, 255)",
+			"hc_black": ".hc-black.vscode-theme-defaults-themes-hc_black-json .token.storage.type rgb(86, 156, 214)"
+		}
+	},
+	{
+		"c": " ",
+		"t": "block.decl.expr.function.meta.ts.var",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "foo",
+		"t": "block.decl.expr.function.meta.ts.var.var-single-variable.variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.variable rgb(156, 220, 254)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.variable rgb(0, 16, 128)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": " = ",
+		"t": "block.decl.expr.function.meta.ts.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "()",
+		"t": "block.brace.decl.expr.function.meta.paren.ts.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": ": ",
+		"t": "annotation.block.decl.expr.function.meta.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "any",
+		"t": "annotation.block.decl.expr.function.meta.primitive.support.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": " ",
+		"t": "annotation.block.decl.expr.function.meta.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "=>",
+		"t": "annotation.block.decl.expr.function.keyword.meta.operator.return.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark.vscode-theme-defaults-themes-dark_vs-json .token.keyword.operator rgb(212, 212, 212)",
+			"light_vs": ".vs.vscode-theme-defaults-themes-light_vs-json .token.keyword.operator rgb(0, 0, 0)",
+			"hc_black": ".hc-black.vscode-theme-defaults-themes-hc_black-json .token.keyword.operator rgb(212, 212, 212)"
+		}
+	},
+	{
+		"c": " (",
+		"t": "annotation.block.cover.decl.expr.function.meta.paren.return.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "{",
+		"t": "annotation.block.brace.cover.curly.decl.expr.function.meta.object.paren.return.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": " ",
+		"t": "annotation.block.cover.decl.declaration.expr.field.function.meta.object.paren.return.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "'bar'",
+		"t": "annotation.block.cover.decl.declaration.expr.field.function.meta.object.paren.return.ts.type.var.var-single-variable.variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": ": ",
+		"t": "annotation.block.cover.decl.declaration.expr.field.function.meta.object.paren.return.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "'baz'",
+		"t": "annotation.block.cover.decl.declaration.expr.field.function.meta.object.paren.return.single.string.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark.vscode-theme-defaults-themes-dark_vs-json .token.string rgb(206, 145, 120)",
+			"light_vs": ".vs.vscode-theme-defaults-themes-light_vs-json .token.string rgb(163, 21, 21)",
+			"hc_black": ".hc-black.vscode-theme-defaults-themes-hc_black-json .token.string rgb(206, 145, 120)"
+		}
+	},
+	{
+		"c": " ",
+		"t": "annotation.block.cover.decl.declaration.expr.field.function.meta.object.paren.return.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "}",
+		"t": "annotation.block.brace.cover.curly.decl.expr.function.meta.object.paren.return.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": ")",
+		"t": "annotation.block.cover.decl.expr.function.meta.paren.return.ts.type.var.var-single-variable",
+		"r": {
+			"dark_plus": ".vs-dark.vscode-theme-defaults-themes-dark_plus-json .token.meta.type.annotation rgb(78, 201, 176)",
+			"light_plus": ".vs.vscode-theme-defaults-themes-light_plus-json .token.meta.type.annotation rgb(38, 127, 153)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	},
+	{
+		"c": "}",
+		"t": "block.brace.curly.decl.function.meta.ts",
+		"r": {
+			"dark_plus": ".vs-dark .token rgb(212, 212, 212)",
+			"light_plus": ".vs .token rgb(0, 0, 0)",
+			"dark_vs": ".vs-dark .token rgb(212, 212, 212)",
+			"light_vs": ".vs .token rgb(0, 0, 0)",
+			"hc_black": ".hc-black .token rgb(255, 255, 255)"
+		}
+	}
+]
\ No newline at end of file