diff --git a/src/compiler/compiler.ts b/src/compiler/compiler.ts
index 11105cd..7a6e005 100644
--- a/src/compiler/compiler.ts
+++ b/src/compiler/compiler.ts
@@ -581,12 +581,14 @@ export class Compiler {
         )
       }
 
-      case terms.Throw: {
+      case terms.Throw:
+      case terms.Not: {
+        const keyword = node.type.id === terms.Throw ? 'Throw' : 'Not'
         const children = getAllChildren(node)
         const [_throwKeyword, expression] = children
         if (!expression) {
           throw new CompilerError(
-            `Throw expected expression, got ${children.length} children`,
+            `${keyword} expected expression, got ${children.length} children`,
             node.from,
             node.to
           )
@@ -594,7 +596,7 @@ export class Compiler {
 
         const instructions: ProgramItem[] = []
         instructions.push(...this.#compileNode(expression, input))
-        instructions.push(['THROW'])
+        instructions.push([keyword.toUpperCase()]) // THROW or NOT
 
         return instructions
       }
diff --git a/src/parser/node.ts b/src/parser/node.ts
index 1bea752..8816fe4 100644
--- a/src/parser/node.ts
+++ b/src/parser/node.ts
@@ -51,6 +51,7 @@ export type NodeType =
   | 'FinallyExpr'
   | 'Throw'
 
+  | 'Not'
   | 'Eq'
   | 'Modulo'
   | 'Plus'
@@ -275,6 +276,9 @@ class SyntaxNodeType {
       case 'Throw':
         return term.Throw
 
+      case 'Not':
+        return term.Not
+
       case 'Eq':
         return term.Eq
 
diff --git a/src/parser/parser2.ts b/src/parser/parser2.ts
index 57ea905..e96fa42 100644
--- a/src/parser/parser2.ts
+++ b/src/parser/parser2.ts
@@ -216,6 +216,9 @@ export class Parser {
     if (this.is($T.Keyword, 'throw'))
       return this.throw()
 
+    if (this.is($T.Keyword, 'not'))
+      return this.not()
+
     if (this.is($T.Keyword, 'import'))
       return this.import()
 
@@ -307,7 +310,7 @@ export class Parser {
         break
       }
 
-      // [ a = true ] 
+      // [ a = true ]
       const next = this.peek(peek)
       if (next?.type === $T.Operator && next.value === '=') {
         isDict = true
@@ -760,6 +763,14 @@ export class Parser {
     return node.push(prefix, val)
   }
 
+  // not blah
+  not(): SyntaxNode {
+    const keyword = this.keyword('not')
+    const val = this.expression()
+    const node = new SyntaxNode('Not', keyword.from, val.to)
+    return node.push(keyword, val)
+  }
+
   // operators like + - =
   op(op?: string): SyntaxNode {
     const token = op ? this.expect($T.Operator, op) : this.expect($T.Operator)
diff --git a/src/parser/shrimp.grammar b/src/parser/shrimp.grammar
index 4f2e032..e7cd9ee 100644
--- a/src/parser/shrimp.grammar
+++ b/src/parser/shrimp.grammar
@@ -44,6 +44,7 @@ try { @specialize[@name=keyword]<Identifier, "try"> }
 catch { @specialize[@name=keyword]<Identifier, "catch"> }
 finally { @specialize[@name=keyword]<Identifier, "finally"> }
 throw { @specialize[@name=keyword]<Identifier, "throw"> }
+not { @specialize[@name=keyword]<Identifier, "not"> }
 import { @specialize[@name=keyword]<Identifier, "import"> }
 null { @specialize[@name=Null]<Identifier, "null"> }
 
@@ -77,6 +78,7 @@ consumeToTerminator {
   ambiguousFunctionCall |
   TryExpr |
   Throw |
+  Not |
   Import |
   IfExpr |
   FunctionDef |
@@ -167,8 +169,12 @@ Throw {
   throw (BinOp | ConditionalOp | expression)
 }
 
+Not {
+  not (BinOp | ConditionalOp | expression)
+}
+
 // this has to be in the parse tree so the scope tracker can use it
-Import { 
+Import {
   import NamedArg* Identifier+ NamedArg*
 }
 
@@ -247,7 +253,7 @@ expression {
     Dollar dot (DotGet | Number | Identifier | ParenExpr)
   }
 
-  String { 
+  String {
     "'" stringContent* "'" | CurlyString | DoubleQuote
   }
 }
diff --git a/src/parser/shrimp.terms.ts b/src/parser/shrimp.terms.ts
index cc00537..c0c8482 100644
--- a/src/parser/shrimp.terms.ts
+++ b/src/parser/shrimp.terms.ts
@@ -32,14 +32,14 @@ export const
   Word = 30,
   IdentifierBeforeDot = 31,
   CurlyString = 32,
-  newline = 101,
-  pipeStartsLine = 102,
+  newline = 103,
+  pipeStartsLine = 104,
   Do = 33,
   Comment = 34,
   Program = 35,
   PipeExpr = 36,
   WhileExpr = 38,
-  keyword = 84,
+  keyword = 86,
   ConditionalOp = 40,
   ParenExpr = 41,
   FunctionCallWithNewlines = 42,
@@ -76,6 +76,7 @@ export const
   FunctionCallWithBlock = 78,
   TryExpr = 79,
   Throw = 81,
-  Import = 83,
-  CompoundAssign = 85,
-  Assign = 86
+  Not = 83,
+  Import = 85,
+  CompoundAssign = 87,
+  Assign = 88
diff --git a/src/parser/shrimp.ts b/src/parser/shrimp.ts
index 7064a86..d99da52 100644
--- a/src/parser/shrimp.ts
+++ b/src/parser/shrimp.ts
@@ -4,14 +4,14 @@ import {operatorTokenizer} from "./operatorTokenizer"
 import {tokenizer, pipeStartsLineTokenizer, specializeKeyword} from "./tokenizer"
 import {trackScope} from "./parserScopeContext"
 import {highlighting} from "./highlight"
-const spec_Identifier = {__proto__:null,while:78, null:116, catch:122, finally:128, end:130, if:138, else:144, try:160, throw:164, import:168}
+const spec_Identifier = {__proto__:null,while:78, null:116, catch:122, finally:128, end:130, if:138, else:144, try:160, throw:164, not:168, import:172}
 export const parser = LRParser.deserialize({
   version: 14,
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+  nodeNames: "⚠ Star Slash Plus Minus And Or Eq EqEq Neq Lt Lte Gt Gte Modulo PlusEq MinusEq StarEq SlashEq ModuloEq Band Bor Bxor Shl Shr Ushr NullishCoalesce NullishEq Identifier AssignableIdentifier Word IdentifierBeforeDot CurlyString Do Comment Program PipeExpr operator WhileExpr keyword ConditionalOp ParenExpr FunctionCall DotGet Number Dollar PositionalArg FunctionDef Params NamedParam NamedArgPrefix String StringFragment Interpolation FunctionCallOrIdentifier EscapeSeq DoubleQuote Boolean Null colon CatchExpr keyword Block FinallyExpr keyword keyword Underscore NamedArg IfExpr keyword FunctionCall ElseIfExpr keyword ElseExpr BinOp Regex Dict Array FunctionCallWithBlock TryExpr keyword Throw keyword Not keyword Import keyword CompoundAssign Assign",
+  maxTerm: 130,
   context: trackScope,
   nodeProps: [
     ["closedBy", 59,"end"]
@@ -19,9 +19,9 @@ export const parser = LRParser.deserialize({
   propSources: [highlighting],
   skippedNodes: [0,34],
   repeatNodeCount: 13,
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-  tokenizers: [operatorTokenizer, 1, 2, 3, tokenizer, pipeStartsLineTokenizer, new LocalTokenGroup("[~RP!O!PU~ZO#d~~", 11)],
+  tokenData: "Lp~R}OX$OXY$mYp$Opq$mqr$Ors%Wst'^tu(uuw$Owx(|xy)Ryz)lz{$O{|*V|}$O}!O*V!O!P$O!P!Q3r!Q!R*w!R![-l![!]<_!]!^<x!^!}$O!}#O=c#O#P?X#P#Q?^#Q#R$O#R#S?w#S#T$O#T#Y@b#Y#ZA|#Z#b@b#b#cGj#c#f@b#f#gHm#g#h@b#h#iIp#i#o@b#o#p$O#p#qLQ#q;'S$O;'S;=`$g<%l~$O~O$O~~LkS$TU!USOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OS$jP;=`<%l$O^$tU!US#^YOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OU%]Z!USOr%Wrs&Ost%Wtu&iuw%Wwx&ix#O%W#O#P&i#P;'S%W;'S;=`'W<%lO%WU&VU!YQ!USOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OQ&lTOr&irs&{s;'S&i;'S;=`'Q<%lO&iQ'QO!YQQ'TP;=`<%l&iU'ZP;=`<%l%W^'eZrY!USOY'^YZ$OZt'^tu(Wuw'^wx(Wx#O'^#O#P(W#P;'S'^;'S;=`(o<%lO'^Y(]SrYOY(WZ;'S(W;'S;=`(i<%lO(WY(lP;=`<%l(W^(rP;=`<%l'^^(|O#j[}Q~)RO#h~U)YU!US#eQOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OU)sU!US#rQOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OU*[X!USOt$Ouw$Ox!Q$O!Q!R*w!R![-l![#O$O#P;'S$O;'S;=`$g<%lO$OU+Ob!US|QOt$Ouw$Ox!O$O!O!P,W!P!Q$O!Q![-l![#O$O#P#R$O#R#S.i#S#U$O#U#V/W#V#c$O#c#d0l#d#l$O#l#m1z#m;'S$O;'S;=`$g<%lO$OU,]W!USOt$Ouw$Ox!Q$O!Q![,u![#O$O#P;'S$O;'S;=`$g<%lO$OU,|Y!US|QOt$Ouw$Ox!Q$O!Q![,u![#O$O#P#R$O#R#S,W#S;'S$O;'S;=`$g<%lO$OU-s[!US|QOt$Ouw$Ox!O$O!O!P,W!P!Q$O!Q![-l![#O$O#P#R$O#R#S.i#S;'S$O;'S;=`$g<%lO$OU.nW!USOt$Ouw$Ox!Q$O!Q![-l![#O$O#P;'S$O;'S;=`$g<%lO$OU/]X!USOt$Ouw$Ox!Q$O!Q!R/x!R!S/x!S#O$O#P;'S$O;'S;=`$g<%lO$OU0PX!US|QOt$Ouw$Ox!Q$O!Q!R/x!R!S/x!S#O$O#P;'S$O;'S;=`$g<%lO$OU0qW!USOt$Ouw$Ox!Q$O!Q!Y1Z!Y#O$O#P;'S$O;'S;=`$g<%lO$OU1bW!US|QOt$Ouw$Ox!Q$O!Q!Y1Z!Y#O$O#P;'S$O;'S;=`$g<%lO$OU2P[!USOt$Ouw$Ox!Q$O!Q![2u![!c$O!c!i2u!i#O$O#P#T$O#T#Z2u#Z;'S$O;'S;=`$g<%lO$OU2|[!US|QOt$Ouw$Ox!Q$O!Q![2u![!c$O!c!i2u!i#O$O#P#T$O#T#Z2u#Z;'S$O;'S;=`$g<%lO$OU3wW!USOt$Ouw$Ox!P$O!P!Q4a!Q#O$O#P;'S$O;'S;=`$g<%lO$OU4f^!USOY5bYZ$OZt5btu6euw5bwx6ex!P5b!P!Q$O!Q!}5b!}#O;W#O#P8s#P;'S5b;'S;=`<X<%lO5bU5i^!US!mQOY5bYZ$OZt5btu6euw5bwx6ex!P5b!P!Q9Y!Q!}5b!}#O;W#O#P8s#P;'S5b;'S;=`<X<%lO5bQ6jX!mQOY6eZ!P6e!P!Q7V!Q!}6e!}#O7t#O#P8s#P;'S6e;'S;=`9S<%lO6eQ7YP!P!Q7]Q7bU!mQ#Z#[7]#]#^7]#a#b7]#g#h7]#i#j7]#m#n7]Q7wVOY7tZ#O7t#O#P8^#P#Q6e#Q;'S7t;'S;=`8m<%lO7tQ8aSOY7tZ;'S7t;'S;=`8m<%lO7tQ8pP;=`<%l7tQ8vSOY6eZ;'S6e;'S;=`9S<%lO6eQ9VP;=`<%l6eU9_W!USOt$Ouw$Ox!P$O!P!Q9w!Q#O$O#P;'S$O;'S;=`$g<%lO$OU:Ob!US!mQOt$Ouw$Ox#O$O#P#Z$O#Z#[9w#[#]$O#]#^9w#^#a$O#a#b9w#b#g$O#g#h9w#h#i$O#i#j9w#j#m$O#m#n9w#n;'S$O;'S;=`$g<%lO$OU;][!USOY;WYZ$OZt;Wtu7tuw;Wwx7tx#O;W#O#P8^#P#Q5b#Q;'S;W;'S;=`<R<%lO;WU<UP;=`<%l;WU<[P;=`<%l5bU<fU!US!]QOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OU=PU!US#bQOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OU=jW#tQ!USOt$Ouw$Ox!_$O!_!`>S!`#O$O#P;'S$O;'S;=`$g<%lO$OU>XV!USOt$Ouw$Ox#O$O#P#Q>n#Q;'S$O;'S;=`$g<%lO$OU>uU#sQ!USOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$O~?^O#k~U?eU#uQ!USOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OU@OU!US!dQOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OU@g^!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#o@b#o;'S$O;'S;=`$g<%lO$OUAjU!SQ!USOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$OUBR_!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#UCQ#U#o@b#o;'S$O;'S;=`$g<%lO$OUCV`!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#`@b#`#aDX#a#o@b#o;'S$O;'S;=`$g<%lO$OUD^`!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#g@b#g#hE`#h#o@b#o;'S$O;'S;=`$g<%lO$OUEe`!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#X@b#X#YFg#Y#o@b#o;'S$O;'S;=`$g<%lO$OUFn^!ZQ!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#o@b#o;'S$O;'S;=`$g<%lO$O^Gq^#lW!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#o@b#o;'S$O;'S;=`$g<%lO$O^Ht^#nW!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#o@b#o;'S$O;'S;=`$g<%lO$O^Iw`#mW!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#f@b#f#gJy#g#o@b#o;'S$O;'S;=`$g<%lO$OUKO`!USOt$Ouw$Ox}$O}!O@b!O!Q$O!Q![@b![!_$O!_!`Ac!`#O$O#P#T$O#T#i@b#i#jE`#j#o@b#o;'S$O;'S;=`$g<%lO$OULXUuQ!USOt$Ouw$Ox#O$O#P;'S$O;'S;=`$g<%lO$O~LpO#v~",
+  tokenizers: [operatorTokenizer, 1, 2, 3, tokenizer, pipeStartsLineTokenizer, new LocalTokenGroup("[~RP!O!PU~ZO#f~~", 11)],
   topRules: {"Program":[0,35]},
   specialized: [{term: 28, get: (value: any, stack: any) => (specializeKeyword(value, stack) << 1), external: specializeKeyword},{term: 28, get: (value: keyof typeof spec_Identifier) => spec_Identifier[value] || -1}],
-  tokenPrec: 2589
+  tokenPrec: 2711
 })
diff --git a/src/parser/tests/tokens.test.ts b/src/parser/tests/tokens.test.ts
index b166570..4d46790 100644
--- a/src/parser/tests/tokens.test.ts
+++ b/src/parser/tests/tokens.test.ts
@@ -304,6 +304,7 @@ describe('keywords', () => {
     expect(`catch`).toMatchToken('Keyword', 'catch')
     expect(`finally`).toMatchToken('Keyword', 'finally')
     expect(`throw`).toMatchToken('Keyword', 'throw')
+    expect(`not`).toMatchToken('Keyword', 'not')
   })
 })
 
diff --git a/src/parser/tokenizer2.ts b/src/parser/tokenizer2.ts
index dacaaca..fd51077 100644
--- a/src/parser/tokenizer2.ts
+++ b/src/parser/tokenizer2.ts
@@ -104,6 +104,7 @@ const keywords = new Set([
   'catch',
   'finally',
   'throw',
+  'not',
 ])
 
 // helper
diff --git a/src/prelude/index.ts b/src/prelude/index.ts
index d69cfc4..c0fb87b 100644
--- a/src/prelude/index.ts
+++ b/src/prelude/index.ts
@@ -89,7 +89,6 @@ export const globals: Record<string, any> = {
   'some?': (v: any) => toValue(v).type !== 'null',
 
   // boolean/logic
-  not: (v: any) => !v,
   bnot: (n: number) => ~(n | 0),
 
   // utilities
diff --git a/src/prelude/tests/prelude.test.ts b/src/prelude/tests/prelude.test.ts
index b297b6a..a260489 100644
--- a/src/prelude/tests/prelude.test.ts
+++ b/src/prelude/tests/prelude.test.ts
@@ -117,6 +117,17 @@ describe('boolean logic', () => {
     await expect(`not 42`).toEvaluateTo(false)
     await expect(`not null`).toEvaluateTo(true)
   })
+
+  test('not works with function calls', async () => {
+    await expect(`equals = do x y: x == y end; not equals 5 5`).toEvaluateTo(false)
+    await expect(`equals = do x y: x == y end; not equals 5 10`).toEvaluateTo(true)
+  })
+
+  test('not works with binary operations and comparisons', async () => {
+    await expect(`not 5 > 10`).toEvaluateTo(true)
+    await expect(`not 10 > 5`).toEvaluateTo(false)
+    await expect(`not true and false`).toEvaluateTo(true)
+  })
 })
 
 describe('utilities', () => {