From def4c601818f2032bdcc3d989c53512de760bcc6 Mon Sep 17 00:00:00 2001
From: Claude <noreply@anthropic.com>
Date: Fri, 23 Jan 2026 19:18:42 +0000
Subject: [PATCH 1/2] Update syntax highlighting with all keywords from
 pytrilogy lark grammar

Updated the VS Code extension's syntax highlighting to cover all grammatical
keywords from the pytrilogy lark grammar file. Changes include:

- Added all statement keywords: select, from, where, having, order, limit, etc.
- Added multi-select keywords: merge, align, derive, rowset, with
- Added persist/copy keywords: persist, append, overwrite, into, copy, csv, json, parquet
- Added datasource keywords: datasource, grain, address, query, file, freshness, etc.
- Added chart keywords: chart, line, bar, barh, point, area, headline, donut, etc.
- Added CASE/WHEN conditional keywords
- Added concept types: key, metric, property, parameter, param, const, constant, unique
- Added all data types: string, number, numeric, int, bigint, date, datetime, timestamp, float, bool, any, struct, list, array, map, tuple
- Added categorized builtin functions: math, string, array, map, aggregate, date, window
- Added operators: <-, ->, ::, between, like, ilike
- Added lambda transform syntax: @identifier
- Added hash types: md5, sha1, sha256, sha512
- Added date parts: DAY, WEEK, MONTH, QUARTER, YEAR, MINUTE, HOUR, SECOND, DAY_OF_WEEK
- Added support for // comments in addition to # comments
- Updated literals to use true, false, null (case-insensitive)
- Made all keyword matching case-insensitive to match lark grammar

https://claude.ai/code/session_01KJrcKzNukbgAV2RGQtWZxX
---
 .../vscode/syntaxes/trilogy.tmLanguage.json   | 192 +++++++++++++-----
 1 file changed, 143 insertions(+), 49 deletions(-)

diff --git a/editors/vscode/syntaxes/trilogy.tmLanguage.json b/editors/vscode/syntaxes/trilogy.tmLanguage.json
index ec574a5..f9fb6c2 100644
--- a/editors/vscode/syntaxes/trilogy.tmLanguage.json
+++ b/editors/vscode/syntaxes/trilogy.tmLanguage.json
@@ -80,7 +80,7 @@
 		"concept-declaration": {
 			"name": "meta.function.trilogy",
 			"patterns": [{
-			"begin": "(?x)\n  \\s*\n  \\b(auto|property|metric|key)\\s+\n    (?=\n    [[:alpha:]_][[:word:]]* \\s* [[:alpha:]_][[:word:]]*    )\n",
+			"begin": "(?ix)\n  \\s*\n  \\b(auto|property|metric|key|parameter|param|const|constant|unique)\\s+\n    (?=\n    [[:alpha:]_][[:word:]]* \\s* [[:alpha:]_][[:word:]]*    )\n",
 			"end": "(:|(?=[#'\"\\n]))",
 			"beginCaptures": {
 				"1": {
@@ -107,7 +107,7 @@
 				}
 			]
 		},{
-			"begin": "(?x)\n  \\s*\n  \\b(auto|property|metric|key)\\s+\n    (?=\n    <\\S+>\\.[[:alpha:]_][[:word:]]* \\s* [[:alpha:]_][[:word:]]*    )\n",
+			"begin": "(?ix)\n  \\s*\n  \\b(auto|property|metric|key|parameter|param|const|constant|unique)\\s+\n    (?=\n    <\\S+>\\.[[:alpha:]_][[:word:]]* \\s* [[:alpha:]_][[:word:]]*    )\n",
 			"end": "(;)",
 			"beginCaptures": {
 				"1": {
@@ -145,10 +145,20 @@
 					"end": "\\n",
 					"beginCaptures": {
 						"0": {
-							"name": "punctuation.definition.comment"
+							"name": "punctuation.definition.comment.hash.trilogy"
 						}
 					},
-					"name": "comment.line.hash"
+					"name": "comment.line.hash.trilogy"
+				},
+				{
+					"begin": "//",
+					"end": "\\n",
+					"beginCaptures": {
+						"0": {
+							"name": "punctuation.definition.comment.double-slash.trilogy"
+						}
+					},
+					"name": "comment.line.double-slash.trilogy"
 				}
 			]
 		},
@@ -289,41 +299,65 @@
 			"patterns": [
 				{
 					"name": "storage.type.function.trilogy",
-					"match": "\\b((async\\s+)?\\s*def)\\b"
+					"match": "(?i)\\b(def)\\b"
+				},
+				{
+					"name": "keyword.control.import.trilogy",
+					"match": "(?i)\\b(?<!\\.)as\\b"
+				},
+				{
+					"name": "keyword.control.select.trilogy",
+					"match": "(?i)\\b(?<!\\.)(select)\\b"
 				},
 				{
 					"name": "keyword.control.flow.trilogy",
-					"comment": "if `as` is eventually followed by `:` or line continuation\nit's probably control flow like:\n    with foo as bar, \\\n         Foo as Bar:\n      try:\n        do_stuff()\n      except Exception as e:\n        pass\n",
-					"match": "\\b(?<!\\.)as\\b(?=.*[:\\\\])"
+					"comment": "Primary query keywords",
+					"match": "(?i)\\b(?<!\\.)(from|where|having|order|limit|by)\\b"
 				},
 				{
-					"name": "keyword.control.import.trilogy",
-					"comment": "other legal use of `as` is in an import",
-					"match": "\\b(?<!\\.)as\\b"
+					"name": "keyword.control.flow.trilogy",
+					"comment": "Multi-select and merge keywords",
+					"match": "(?i)\\b(?<!\\.)(merge|align|derive|rowset|with)\\b"
 				},
-								{
-					"name": "keyword.control.select.trilogy",
-					"match": "(?i)(?x)\n  \\b(?<!\\.)(\n    select  )\\b\n"
+				{
+					"name": "keyword.control.flow.trilogy",
+					"comment": "Persist and data operation keywords",
+					"match": "(?i)\\b(?<!\\.)(persist|append|overwrite|into|copy|csv|json|parquet)\\b"
 				},
 				{
 					"name": "keyword.control.flow.trilogy",
-					"match": "(?i)(?x)\n  \\b(?<!\\.)(\n   raw_sql | async | continue | select | del | assert | persist | into | break | finally | for\n    | from | elif | else | if | except | pass | raise\n    | return | try | while | with | datasource | root\n  )\\b\n"
+					"comment": "Datasource keywords",
+					"match": "(?i)\\b(?<!\\.)(datasource|grain|address|query|file|freshness|complete|root|partition|incremental|state|published|unpublished)\\b"
 				},
 				{
-					"name": "storage.modifier.declaration.trilogy",
-					"match": "(?x)\n  \\b(?<!\\.)(\n    global | nonlocal\n  )\\b\n"
+					"name": "keyword.control.flow.trilogy",
+					"comment": "Statement keywords",
+					"match": "(?i)\\b(?<!\\.)(raw_sql|validate|mock|publish|unpublish|create|show|type|drop)\\b"
 				},
 				{
-					"name": "storage.type.class.trilogy",
-					"match": "\\b(?<!\\.)(class)\\b"
+					"name": "keyword.control.flow.trilogy",
+					"comment": "Chart keywords",
+					"match": "(?i)\\b(?<!\\.)(chart|line|bar|barh|point|area|headline|donut|heatmap|boxplot|treemap|set|x_axis|y_axis|color|size|group|trellis|trellis_row|geo|annotation|hide_legend|show_title|scale_x|scale_y|linear|sqrt)\\b"
 				},
 				{
-					"match": "(?x)\n  ^\\s*(\n    case | match\n  )(?=\\s*([-+\\w\\d(\\[{'\":#]|$))\\b\n",
-					"captures": {
-						"1": {
-							"name": "keyword.control.flow.trilogy"
-						}
-					}
+					"name": "keyword.control.conditional.trilogy",
+					"comment": "CASE/WHEN conditional keywords",
+					"match": "(?i)\\b(?<!\\.)(case|when|then|else|end)\\b"
+				},
+				{
+					"name": "keyword.control.filter.trilogy",
+					"comment": "Filter and window keywords",
+					"match": "(?i)\\b(?<!\\.)(filter|over)\\b"
+				},
+				{
+					"name": "keyword.other.order.trilogy",
+					"comment": "Ordering keywords",
+					"match": "(?i)\\b(?<!\\.)(asc|desc|nulls|first|last)\\b"
+				},
+				{
+					"name": "storage.type.concept.trilogy",
+					"comment": "Concept declaration types",
+					"match": "(?i)\\b(?<!\\.)(key|metric|property|parameter|param|const|constant|unique)\\b"
 				}
 			]
 		},
@@ -596,24 +630,62 @@
 		},
 		"builtin-types": {
 			"name": "support.type.trilogy",
-			"match": "(?x)\n  (?<!\\.) \\b(\n   string | bool | bytearray | bytes  | float | int | list  |  str | tuple\n  )\\b\n"
+			"match": "(?i)(?<!\\.)\\b(string|number|numeric|int|bigint|date|datetime|timestamp|float|bool|any|struct|list|array|map|tuple)\\b"
 		},
 		"builtin-functions": {
 			"patterns": [
 				{
-					"name": "support.function.builtin.trilogy",
-					"match": "(?x)\n  (?<!\\.) \\b(\n  abs | all | any  |  divmod | where | filter | format | row_number |  hash | id |  len\n    | max |  min | avg | pow   |  round | order | sum | count  )\\b\n"
+					"name": "support.function.math.trilogy",
+					"comment": "Mathematical functions",
+					"match": "(?i)(?<!\\.)\\b(add|subtract|multiply|divide|mod|log|round|floor|ceil|abs|sqrt|random)\\b"
+				},
+				{
+					"name": "support.function.string.trilogy",
+					"comment": "String functions",
+					"match": "(?i)(?<!\\.)\\b(like|ilike|upper|lower|split|strpos|substring|contains|trim|replace|regexp_extract|regexp_contains|regexp_replace|hash|concat)\\b"
+				},
+				{
+					"name": "support.function.array.trilogy",
+					"comment": "Array functions",
+					"match": "(?i)(?<!\\.)\\b(array_sum|array_distinct|array_to_string|array_sort|array_transform|array_filter|generate_array|unnest|union|array_agg)\\b"
+				},
+				{
+					"name": "support.function.map.trilogy",
+					"comment": "Map functions",
+					"match": "(?i)(?<!\\.)\\b(map_keys|map_values)\\b"
+				},
+				{
+					"name": "support.function.generic.trilogy",
+					"comment": "Generic functions",
+					"match": "(?i)(?<!\\.)\\b(cast|coalesce|nullif|len|bool|getattr|recurse_edge)\\b"
+				},
+				{
+					"name": "support.function.aggregate.trilogy",
+					"comment": "Aggregate functions",
+					"match": "(?i)(?<!\\.)\\b(count|count_distinct|sum|avg|max|min|bool_and|bool_or|any)\\b"
+				},
+				{
+					"name": "support.function.date.trilogy",
+					"comment": "Date/time functions",
+					"match": "(?i)(?<!\\.)\\b(date|datetime|timestamp|second|minute|hour|day|day_name|day_of_week|week|month|month_name|quarter|year|format_time|parse_time|date_trunc|date_truncate|date_part|date_add|date_sub|date_diff|date_spine)\\b"
+				},
+				{
+					"name": "support.function.constant.trilogy",
+					"comment": "Constant functions",
+					"match": "(?i)(?<!\\.)\\b(current_date|current_datetime|current_timestamp)\\b"
+				},
+				{
+					"name": "support.function.window.trilogy",
+					"comment": "Window functions",
+					"match": "(?i)(?<!\\.)\\b(row_number|rank|lag|lead)\\b"
 				}
 			]
 		},
 		"illegal-names": {
-			"match": "(?x)\n  \\b(?:\n    (\n      and |  def\n   | del | elif | where | else | for | from |  if | in | is  |  not | or   ) | (\n      as | import\n    )\n  )\\b\n",
+			"match": "(?i)\\b(and|or|not|in|is|def|where|else|for|from|if|as|import|select|persist|merge|datasource|key|metric|property|const|auto)\\b",
 			"captures": {
 				"1": {
 					"name": "keyword.control.flow.trilogy"
-				},
-				"2": {
-					"name": "keyword.control.import.trilogy"
 				}
 			}
 		},
@@ -825,7 +897,7 @@
 			"patterns": [
 				{
 					"name": "constant.language.trilogy",
-					"match": "\\b(True|False|None|NotImplemented|Ellipsis)\\b"
+					"match": "(?i)\\b(true|false|null)\\b"
 				},
 				{
 					"include": "#number"
@@ -850,27 +922,25 @@
 			]
 		},
 		"operator": {
-			"match": "(?x)\n    \\b(?<!\\.)\n      (?:\n        (and | or | not | in | is)                         (?# 1)\n        |\n        (for | if | else | await | (?:yield(?:\\s+from)?))  (?# 2)\n      )\n    (?!\\s*:)\\b\n\n    | (<< | >> | & | \\| | \\^ | ~)                          (?# 3)\n\n    | (\\*\\* | \\* | \\+ | - | % | // | / | @)                (?# 4)\n\n    | (!= | == | >= | <= | < | >)                          (?# 5)\n\n    | (:=)                                                 (?# 6)\n",
-			"captures": {
-				"1": {
-					"name": "keyword.operator.logical.trilogy"
-				},
-				"2": {
-					"name": "keyword.control.flow.trilogy"
-				},
-				"3": {
-					"name": "keyword.operator.bitwise.trilogy"
+			"patterns": [
+				{
+					"name": "keyword.operator.logical.trilogy",
+					"match": "(?i)\\b(and|or|not|in|is|between|like|ilike)\\b"
 				},
-				"4": {
-					"name": "keyword.operator.arithmetic.trilogy"
+				{
+					"name": "keyword.operator.assignment.trilogy",
+					"comment": "Arrow assignment operators",
+					"match": "<-|->|::"
 				},
-				"5": {
-					"name": "keyword.operator.comparison.trilogy"
+				{
+					"name": "keyword.operator.arithmetic.trilogy",
+					"match": "\\*\\*|\\*|\\+|-|%|/|\\|\\|"
 				},
-				"6": {
-					"name": "keyword.operator.assignment.trilogy"
+				{
+					"name": "keyword.operator.comparison.trilogy",
+					"match": "!=|==|>=|<=|<>|<|>|="
 				}
-			}
+			]
 		},
 		"round-braces": {
 			"begin": "\\(",
@@ -900,6 +970,15 @@
 				{
 					"include": "#string"
 				},
+				{
+					"include": "#lambda-transform"
+				},
+				{
+					"include": "#hash-type"
+				},
+				{
+					"include": "#date-part"
+				},
 				{
 					"include": "#illegal-operator"
 				},
@@ -950,6 +1029,21 @@
 				}
 			]
 		},
+		"lambda-transform": {
+			"comment": "Lambda transform syntax @identifier used in array_transform and array_filter",
+			"name": "variable.parameter.lambda.trilogy",
+			"match": "@[[:alpha:]_][[:word:]]*"
+		},
+		"hash-type": {
+			"comment": "Hash algorithm types",
+			"name": "constant.other.hash-type.trilogy",
+			"match": "(?i)\\b(md5|sha1|sha256|sha512)\\b"
+		},
+		"date-part": {
+			"comment": "Date part constants used in date functions",
+			"name": "constant.other.date-part.trilogy",
+			"match": "(?i)\\b(DAY|WEEK|MONTH|QUARTER|YEAR|MINUTE|HOUR|SECOND|DAY_OF_WEEK)\\b"
+		},
 		"odd-function-call": {
 			"comment": "A bit obscured function call where there may have been an\narbitrary number of other operations to get the function.\nE.g. \"arr[idx](args)\"\n",
 			"begin": "(?x)\n  (?<= \\] | \\) ) \\s*\n  (?=\\()\n",

From 5c7550005016aacf91ca30211f0a3a22627bd539 Mon Sep 17 00:00:00 2001
From: Claude <noreply@anthropic.com>
Date: Fri, 23 Jan 2026 19:26:44 +0000
Subject: [PATCH 2/2] Bump version to 0.1.27 and add comprehensive syntax
 highlighting tests

- Bump extension version from 0.1.26 to 0.1.27
- Add grammar tests for keywords, concepts, functions, types, operators, literals, comments
- Fix sqrt being incorrectly included in chart keywords (it's a math function)
- Fix || being incorrectly marked as invalid operator (it's string concatenation)
- Add import keyword to statement-keyword patterns

Test coverage includes:
- Query keywords (select, from, where, having, order, limit, by)
- Multi-select keywords (merge, align, derive, rowset, with)
- Persist/copy keywords (persist, append, overwrite, into, copy, csv, json, parquet)
- Datasource keywords (datasource, grain, address, query, file, etc.)
- Chart keywords (chart, line, bar, point, area, etc.)
- CASE/WHEN conditionals
- Concept types (key, metric, property, parameter, const, unique)
- Data types (string, number, int, bigint, float, struct, list, array, map)
- Functions (math, string, array, map, aggregate, date, window, constants)
- Operators (logical, assignment, arithmetic, comparison)
- Literals (true/false/null, lambda transforms, hash types, date parts, numbers, strings)
- Comments (# and //)

https://claude.ai/code/session_01KJrcKzNukbgAV2RGQtWZxX
---
 editors/vscode/package.json                   |   2 +-
 .../src/test/grammar/comments.test.preql      |   7 +
 .../src/test/grammar/concepts.test.preql      |  29 ++++
 .../src/test/grammar/functions.test.preql     | 145 ++++++++++++++++
 .../src/test/grammar/keywords.test.preql      | 159 ++++++++++++++++++
 .../src/test/grammar/literals.test.preql      |  79 +++++++++
 .../src/test/grammar/operators.test.preql     |  57 +++++++
 .../vscode/src/test/grammar/types.test.preql  |  37 ++++
 .../vscode/syntaxes/trilogy.tmLanguage.json   |  10 +-
 9 files changed, 517 insertions(+), 8 deletions(-)
 create mode 100644 editors/vscode/src/test/grammar/comments.test.preql
 create mode 100644 editors/vscode/src/test/grammar/concepts.test.preql
 create mode 100644 editors/vscode/src/test/grammar/functions.test.preql
 create mode 100644 editors/vscode/src/test/grammar/keywords.test.preql
 create mode 100644 editors/vscode/src/test/grammar/literals.test.preql
 create mode 100644 editors/vscode/src/test/grammar/operators.test.preql
 create mode 100644 editors/vscode/src/test/grammar/types.test.preql

diff --git a/editors/vscode/package.json b/editors/vscode/package.json
index b0e8c65..d6a9de3 100644
--- a/editors/vscode/package.json
+++ b/editors/vscode/package.json
@@ -4,7 +4,7 @@
 	"author": "N/A",
 	"repository": "https://github.com/trilogydata/trilogy-language-server",
 	"license": "MIT",
-	"version": "0.1.26",
+	"version": "0.1.27",
 	"publisher": "trilogydata",
 	"engines": {
 		"vscode": "^1.73.0"
diff --git a/editors/vscode/src/test/grammar/comments.test.preql b/editors/vscode/src/test/grammar/comments.test.preql
new file mode 100644
index 0000000..6689d0c
--- /dev/null
+++ b/editors/vscode/src/test/grammar/comments.test.preql
@@ -0,0 +1,7 @@
+# SYNTAX TEST "source.trilogy" "comments syntax highlighting"
+
+# This is a hash comment
+# <----------------------  comment.line.hash.trilogy
+
+// This is a double-slash comment
+# <-----------------------------  comment.line.double-slash.trilogy
diff --git a/editors/vscode/src/test/grammar/concepts.test.preql b/editors/vscode/src/test/grammar/concepts.test.preql
new file mode 100644
index 0000000..2ee1f90
--- /dev/null
+++ b/editors/vscode/src/test/grammar/concepts.test.preql
@@ -0,0 +1,29 @@
+# SYNTAX TEST "source.trilogy" "concept types syntax highlighting"
+
+# Test: Concept declaration types (standalone)
+KEY
+# <--  storage.type.concept.trilogy
+METRIC
+# <-----  storage.type.concept.trilogy
+PROPERTY
+# <-------  storage.type.concept.trilogy
+PARAMETER
+# <--------  storage.type.concept.trilogy
+PARAM
+# <----  storage.type.concept.trilogy
+CONST
+# <----  storage.type.concept.trilogy
+CONSTANT
+# <-------  storage.type.concept.trilogy
+UNIQUE
+# <-----  storage.type.concept.trilogy
+
+# Test: Case insensitivity
+key
+# <--  storage.type.concept.trilogy
+metric
+# <-----  storage.type.concept.trilogy
+property
+# <-------  storage.type.concept.trilogy
+const
+# <----  storage.type.concept.trilogy
diff --git a/editors/vscode/src/test/grammar/functions.test.preql b/editors/vscode/src/test/grammar/functions.test.preql
new file mode 100644
index 0000000..d638bf7
--- /dev/null
+++ b/editors/vscode/src/test/grammar/functions.test.preql
@@ -0,0 +1,145 @@
+# SYNTAX TEST "source.trilogy" "functions syntax highlighting"
+
+# Test: Mathematical functions
+ABS
+# <--  support.function.math.trilogy
+SQRT
+# <---  support.function.math.trilogy
+ROUND
+# <----  support.function.math.trilogy
+FLOOR
+# <----  support.function.math.trilogy
+CEIL
+# <---  support.function.math.trilogy
+LOG
+# <--  support.function.math.trilogy
+MOD
+# <--  support.function.math.trilogy
+RANDOM
+# <-----  support.function.math.trilogy
+
+# Test: String functions
+UPPER
+# <----  support.function.string.trilogy
+LOWER
+# <----  support.function.string.trilogy
+SPLIT
+# <----  support.function.string.trilogy
+STRPOS
+# <-----  support.function.string.trilogy
+SUBSTRING
+# <--------  support.function.string.trilogy
+CONTAINS
+# <-------  support.function.string.trilogy
+TRIM
+# <---  support.function.string.trilogy
+REPLACE
+# <------  support.function.string.trilogy
+CONCAT
+# <-----  support.function.string.trilogy
+REGEXP_EXTRACT
+# <------------  support.function.string.trilogy
+REGEXP_CONTAINS
+# <-------------  support.function.string.trilogy
+REGEXP_REPLACE
+# <------------  support.function.string.trilogy
+HASH
+# <---  support.function.string.trilogy
+
+# Test: Array functions
+ARRAY_SUM
+# <--------  support.function.array.trilogy
+ARRAY_DISTINCT
+# <-------------  support.function.array.trilogy
+ARRAY_TO_STRING
+# <--------------  support.function.array.trilogy
+ARRAY_SORT
+# <---------  support.function.array.trilogy
+ARRAY_TRANSFORM
+# <--------------  support.function.array.trilogy
+ARRAY_FILTER
+# <-----------  support.function.array.trilogy
+GENERATE_ARRAY
+# <-------------  support.function.array.trilogy
+UNNEST
+# <-----  support.function.array.trilogy
+UNION
+# <----  support.function.array.trilogy
+ARRAY_AGG
+# <--------  support.function.array.trilogy
+
+# Test: Map functions
+MAP_KEYS
+# <-------  support.function.map.trilogy
+MAP_VALUES
+# <---------  support.function.map.trilogy
+
+# Test: Generic functions
+CAST
+# <---  support.function.generic.trilogy
+COALESCE
+# <-------  support.function.generic.trilogy
+NULLIF
+# <-----  support.function.generic.trilogy
+LEN
+# <--  support.function.generic.trilogy
+
+# Test: Aggregate functions
+COUNT
+# <----  support.function.aggregate.trilogy
+COUNT_DISTINCT
+# <-------------  support.function.aggregate.trilogy
+SUM
+# <--  support.function.aggregate.trilogy
+AVG
+# <--  support.function.aggregate.trilogy
+MAX
+# <--  support.function.aggregate.trilogy
+MIN
+# <--  support.function.aggregate.trilogy
+BOOL_AND
+# <-------  support.function.aggregate.trilogy
+BOOL_OR
+# <------  support.function.aggregate.trilogy
+
+# Test: Date/time functions (those that don't overlap with date parts)
+DAY_NAME
+# <-------  support.function.date.trilogy
+MONTH_NAME
+# <---------  support.function.date.trilogy
+FORMAT_TIME
+# <----------  support.function.date.trilogy
+PARSE_TIME
+# <---------  support.function.date.trilogy
+DATE_TRUNC
+# <---------  support.function.date.trilogy
+DATE_TRUNCATE
+# <------------  support.function.date.trilogy
+DATE_PART
+# <--------  support.function.date.trilogy
+DATE_ADD
+# <-------  support.function.date.trilogy
+DATE_SUB
+# <-------  support.function.date.trilogy
+DATE_DIFF
+# <--------  support.function.date.trilogy
+DATE_SPINE
+# <---------  support.function.date.trilogy
+
+# Test: Constant functions
+CURRENT_DATE
+# <-----------  support.function.constant.trilogy
+CURRENT_DATETIME
+# <---------------  support.function.constant.trilogy
+CURRENT_TIMESTAMP
+# <----------------  support.function.constant.trilogy
+
+# Test: Window functions
+ROW_NUMBER
+# <---------  support.function.window.trilogy
+RANK
+# <---  support.function.window.trilogy
+LAG
+# <--  support.function.window.trilogy
+LEAD
+# <---  support.function.window.trilogy
diff --git a/editors/vscode/src/test/grammar/keywords.test.preql b/editors/vscode/src/test/grammar/keywords.test.preql
new file mode 100644
index 0000000..16aa7d9
--- /dev/null
+++ b/editors/vscode/src/test/grammar/keywords.test.preql
@@ -0,0 +1,159 @@
+# SYNTAX TEST "source.trilogy" "keywords syntax highlighting"
+
+# Test: Query keywords
+SELECT
+# <-----  keyword.control.select.trilogy
+FROM
+# <---  keyword.control.flow.trilogy
+WHERE
+# <----  keyword.control.flow.trilogy
+HAVING
+# <-----  keyword.control.flow.trilogy
+ORDER
+# <----  keyword.control.flow.trilogy
+LIMIT
+# <----  keyword.control.flow.trilogy
+BY
+# <-  keyword.control.flow.trilogy
+
+# Test: Multi-select keywords
+MERGE
+# <----  keyword.control.flow.trilogy
+ALIGN
+# <----  keyword.control.flow.trilogy
+DERIVE
+# <-----  keyword.control.flow.trilogy
+ROWSET
+# <-----  keyword.control.flow.trilogy
+WITH
+# <---  keyword.control.flow.trilogy
+
+# Test: Persist and data operation keywords
+PERSIST
+# <------  keyword.control.flow.trilogy
+APPEND
+# <-----  keyword.control.flow.trilogy
+OVERWRITE
+# <--------  keyword.control.flow.trilogy
+INTO
+# <---  keyword.control.flow.trilogy
+COPY
+# <---  keyword.control.flow.trilogy
+CSV
+# <--  keyword.control.flow.trilogy
+JSON
+# <---  keyword.control.flow.trilogy
+PARQUET
+# <------  keyword.control.flow.trilogy
+
+# Test: Datasource keywords
+datasource
+# <---------  keyword.control.flow.trilogy
+GRAIN
+# <----  keyword.control.flow.trilogy
+ADDRESS
+# <------  keyword.control.flow.trilogy
+QUERY
+# <----  keyword.control.flow.trilogy
+FILE
+# <---  keyword.control.flow.trilogy
+FRESHNESS
+# <--------  keyword.control.flow.trilogy
+COMPLETE
+# <-------  keyword.control.flow.trilogy
+ROOT
+# <---  keyword.control.flow.trilogy
+PARTITION
+# <--------  keyword.control.flow.trilogy
+INCREMENTAL
+# <----------  keyword.control.flow.trilogy
+STATE
+# <----  keyword.control.flow.trilogy
+PUBLISHED
+# <--------  keyword.control.flow.trilogy
+UNPUBLISHED
+# <----------  keyword.control.flow.trilogy
+
+# Test: Statement keywords
+RAW_SQL
+# <------  keyword.control.flow.trilogy
+VALIDATE
+# <-------  keyword.control.flow.trilogy
+MOCK
+# <---  keyword.control.flow.trilogy
+PUBLISH
+# <------  keyword.control.flow.trilogy
+UNPUBLISH
+# <--------  keyword.control.flow.trilogy
+CREATE
+# <-----  keyword.control.flow.trilogy
+SHOW
+# <---  keyword.control.flow.trilogy
+TYPE
+# <---  keyword.control.flow.trilogy
+DROP
+# <---  keyword.control.flow.trilogy
+
+# Test: Chart keywords
+CHART
+# <----  keyword.control.flow.trilogy
+LINE
+# <---  keyword.control.flow.trilogy
+BAR
+# <--  keyword.control.flow.trilogy
+BARH
+# <---  keyword.control.flow.trilogy
+POINT
+# <----  keyword.control.flow.trilogy
+AREA
+# <---  keyword.control.flow.trilogy
+HEADLINE
+# <-------  keyword.control.flow.trilogy
+DONUT
+# <----  keyword.control.flow.trilogy
+HEATMAP
+# <------  keyword.control.flow.trilogy
+BOXPLOT
+# <------  keyword.control.flow.trilogy
+TREEMAP
+# <------  keyword.control.flow.trilogy
+
+# Test: CASE/WHEN conditional keywords
+CASE
+# <---  keyword.control.conditional.trilogy
+WHEN
+# <---  keyword.control.conditional.trilogy
+THEN
+# <---  keyword.control.conditional.trilogy
+ELSE
+# <---  keyword.control.conditional.trilogy
+END
+# <--  keyword.control.conditional.trilogy
+
+# Test: Filter and window keywords
+FILTER
+# <-----  keyword.control.filter.trilogy
+OVER
+# <---  keyword.control.filter.trilogy
+
+# Test: Ordering keywords
+ASC
+# <--  keyword.other.order.trilogy
+DESC
+# <---  keyword.other.order.trilogy
+NULLS
+# <----  keyword.other.order.trilogy
+FIRST
+# <----  keyword.other.order.trilogy
+LAST
+# <---  keyword.other.order.trilogy
+
+# Test: Import keywords
+IMPORT
+# <-----  keyword.control.import.trilogy
+AS
+# <-  keyword.control.import.trilogy
+
+# Test: Function definition
+DEF
+# <--  storage.type.function.trilogy
diff --git a/editors/vscode/src/test/grammar/literals.test.preql b/editors/vscode/src/test/grammar/literals.test.preql
new file mode 100644
index 0000000..9bfba09
--- /dev/null
+++ b/editors/vscode/src/test/grammar/literals.test.preql
@@ -0,0 +1,79 @@
+# SYNTAX TEST "source.trilogy" "literals and special syntax highlighting"
+
+# Test: Boolean literals
+TRUE
+# <---  constant.language.trilogy
+FALSE
+# <----  constant.language.trilogy
+true
+# <---  constant.language.trilogy
+false
+# <----  constant.language.trilogy
+True
+# <---  constant.language.trilogy
+False
+# <----  constant.language.trilogy
+
+# Test: Null literal
+NULL
+# <---  constant.language.trilogy
+null
+# <---  constant.language.trilogy
+Null
+# <---  constant.language.trilogy
+
+# Test: Lambda transform syntax
+@item
+# <---  variable.parameter.lambda.trilogy
+@element
+# <------  variable.parameter.lambda.trilogy
+@x
+# <-  variable.parameter.lambda.trilogy
+
+# Test: Hash types
+MD5
+# <--  constant.other.hash-type.trilogy
+SHA1
+# <---  constant.other.hash-type.trilogy
+SHA256
+# <-----  constant.other.hash-type.trilogy
+SHA512
+# <-----  constant.other.hash-type.trilogy
+md5
+# <--  constant.other.hash-type.trilogy
+sha256
+# <-----  constant.other.hash-type.trilogy
+
+# Test: Date parts
+DAY
+# <--  constant.other.date-part.trilogy
+WEEK
+# <---  constant.other.date-part.trilogy
+MONTH
+# <----  constant.other.date-part.trilogy
+QUARTER
+# <------  constant.other.date-part.trilogy
+YEAR
+# <---  constant.other.date-part.trilogy
+MINUTE
+# <-----  constant.other.date-part.trilogy
+HOUR
+# <---  constant.other.date-part.trilogy
+SECOND
+# <-----  constant.other.date-part.trilogy
+DAY_OF_WEEK
+# <----------  constant.other.date-part.trilogy
+
+# Test: Numeric literals
+123
+# <--  constant.numeric.dec.trilogy
+3.14
+# <---  constant.numeric.float.trilogy
+42
+# <-  constant.numeric.dec.trilogy
+
+# Test: String literals
+"hello world"
+# <----------  string.quoted.single.trilogy
+'single quoted'
+# <------------  string.quoted.single.trilogy
diff --git a/editors/vscode/src/test/grammar/operators.test.preql b/editors/vscode/src/test/grammar/operators.test.preql
new file mode 100644
index 0000000..c36dabb
--- /dev/null
+++ b/editors/vscode/src/test/grammar/operators.test.preql
@@ -0,0 +1,57 @@
+# SYNTAX TEST "source.trilogy" "operators syntax highlighting"
+
+# Test: Logical operators
+AND
+# <--  keyword.operator.logical.trilogy
+OR
+# <-  keyword.operator.logical.trilogy
+NOT
+# <--  keyword.operator.logical.trilogy
+IN
+# <-  keyword.operator.logical.trilogy
+IS
+# <-  keyword.operator.logical.trilogy
+BETWEEN
+# <------  keyword.operator.logical.trilogy
+LIKE
+# <---  keyword.operator.logical.trilogy
+ILIKE
+# <----  keyword.operator.logical.trilogy
+
+# Test: Assignment operators
+<-
+# <-  keyword.operator.assignment.trilogy
+->
+# <-  keyword.operator.assignment.trilogy
+::
+# <-  keyword.operator.assignment.trilogy
+
+# Test: Arithmetic operators
+x + y
+# ^ keyword.operator.arithmetic.trilogy
+x - y
+# ^ keyword.operator.arithmetic.trilogy
+x * y
+# ^ keyword.operator.arithmetic.trilogy
+x / y
+# ^ keyword.operator.arithmetic.trilogy
+x % y
+# ^ keyword.operator.arithmetic.trilogy
+x ** y
+# ^^ keyword.operator.arithmetic.trilogy
+x || y
+# ^^ keyword.operator.arithmetic.trilogy
+
+# Test: Comparison operators
+x != y
+# ^^ keyword.operator.comparison.trilogy
+x > y
+# ^ keyword.operator.comparison.trilogy
+x < y
+# ^ keyword.operator.comparison.trilogy
+x >= y
+# ^^ keyword.operator.comparison.trilogy
+x <= y
+# ^^ keyword.operator.comparison.trilogy
+x <> y
+# ^^ keyword.operator.comparison.trilogy
diff --git a/editors/vscode/src/test/grammar/types.test.preql b/editors/vscode/src/test/grammar/types.test.preql
new file mode 100644
index 0000000..59c51d0
--- /dev/null
+++ b/editors/vscode/src/test/grammar/types.test.preql
@@ -0,0 +1,37 @@
+# SYNTAX TEST "source.trilogy" "data types syntax highlighting"
+
+# Test: Basic data types (those that don't overlap with functions)
+STRING
+# <-----  support.type.trilogy
+NUMBER
+# <-----  support.type.trilogy
+NUMERIC
+# <------  support.type.trilogy
+INT
+# <--  support.type.trilogy
+BIGINT
+# <-----  support.type.trilogy
+FLOAT
+# <----  support.type.trilogy
+
+# Test: Complex data types
+STRUCT
+# <-----  support.type.trilogy
+LIST
+# <---  support.type.trilogy
+ARRAY
+# <----  support.type.trilogy
+MAP
+# <--  support.type.trilogy
+TUPLE
+# <----  support.type.trilogy
+
+# Test: Case insensitivity
+string
+# <-----  support.type.trilogy
+int
+# <--  support.type.trilogy
+float
+# <----  support.type.trilogy
+bigint
+# <-----  support.type.trilogy
diff --git a/editors/vscode/syntaxes/trilogy.tmLanguage.json b/editors/vscode/syntaxes/trilogy.tmLanguage.json
index f9fb6c2..7f3e761 100644
--- a/editors/vscode/syntaxes/trilogy.tmLanguage.json
+++ b/editors/vscode/syntaxes/trilogy.tmLanguage.json
@@ -303,7 +303,7 @@
 				},
 				{
 					"name": "keyword.control.import.trilogy",
-					"match": "(?i)\\b(?<!\\.)as\\b"
+					"match": "(?i)\\b(?<!\\.)(as|import)\\b"
 				},
 				{
 					"name": "keyword.control.select.trilogy",
@@ -337,7 +337,7 @@
 				{
 					"name": "keyword.control.flow.trilogy",
 					"comment": "Chart keywords",
-					"match": "(?i)\\b(?<!\\.)(chart|line|bar|barh|point|area|headline|donut|heatmap|boxplot|treemap|set|x_axis|y_axis|color|size|group|trellis|trellis_row|geo|annotation|hide_legend|show_title|scale_x|scale_y|linear|sqrt)\\b"
+					"match": "(?i)\\b(?<!\\.)(chart|line|bar|barh|point|area|headline|donut|heatmap|boxplot|treemap|set|x_axis|y_axis|color|size|group|trellis|trellis_row|geo|annotation|hide_legend|show_title|scale_x|scale_y|linear)\\b"
 				},
 				{
 					"name": "keyword.control.conditional.trilogy",
@@ -908,11 +908,7 @@
 			"patterns": [
 				{
 					"name": "invalid.illegal.operator.trilogy",
-					"match": "&&|\\|\\||--|\\+\\+"
-				},
-				{
-					"name": "invalid.illegal.operator.trilogy",
-					"match": "[?$]"
+					"match": "&&|--|\\+\\+"
 				},
 				{
 					"name": "invalid.illegal.operator.trilogy",