diff --git a/civet.dev/cheatsheet.md b/civet.dev/cheatsheet.md
index 483e4394c..bc2e7d4c9 100644
--- a/civet.dev/cheatsheet.md
+++ b/civet.dev/cheatsheet.md
@@ -319,6 +319,7 @@ a + b = c
 <Playground>
 a is b
 a is not b
+not a
 a and b
 a or b
 a not in b
@@ -326,6 +327,17 @@ a not instanceof b
 a?
 </Playground>
 
+### Two Levels of Precedence
+
+Like Perl, Ruby, and LiveScript, `and`/`or`/`not` have lower precedence
+than `&&`/`||`/`!`/comparisons (unless you [explicitly disable via
+`"civet coffeeAndOrNot"`](#coffeescript-operators)).
+
+<Playground>
+not a == b
+a || b and c || d
+</Playground>
+
 ### Includes Operator
 
 <Playground>
@@ -1440,6 +1452,11 @@ x == y != z
 x isnt y
 </Playground>
 
+<Playground>
+"civet coffeeAndOr"
+a || b and c || d
+</Playground>
+
 <Playground>
 "civet coffeeNot"
 not (x == y)
diff --git a/notes/Comparison-to-CoffeeScript.md b/notes/Comparison-to-CoffeeScript.md
index 7df0c8e82..ba94977d6 100644
--- a/notes/Comparison-to-CoffeeScript.md
+++ b/notes/Comparison-to-CoffeeScript.md
@@ -154,6 +154,7 @@ Civet provides a compatibility prologue directive that aims to be 97+% compatibl
 | Configuration       | What it enables |
 |---------------------|---------------------------------------------------------------------|
 | autoVar             | declare implicit vars based on assignment to undeclared identifiers |
+| coffeeAndOr         | `and` → `&&`, `or` → `||` with same precedence |
 | coffeeBooleans      | `yes`, `no`, `on`, `off` |
 | coffeeComment       | `# single line comments` |
 | coffeeDo            | `do ->`, disables ES6 do/while |
@@ -161,7 +162,7 @@ Civet provides a compatibility prologue directive that aims to be 97+% compatibl
 | coffeeForLoops      | for in, of, from loops behave like they do in CoffeeScript |
 | coffeeInterpolation | `"a string with #{myVar}"` |
 | coffeeIsnt          | `isnt` → `!==` |
-| coffeeNot           | `not` → `!`    |
+| coffeeNot           | `not` → `!` with same precedence |
 | coffeeOf            | `a of b` → `a in b`, `a not of b` → `!(a in b)`, `a in b` → `b.indexOf(a) >= 0`, `a not in b` → `b.indexOf(a) < 0` |
 | coffeePrototype     | enables `x::` -> `x.prototype` and `x::y` -> `x.prototype.y` shorthand.
 
diff --git a/source/lib.js b/source/lib.js
index 69f596001..0cfc276b2 100644
--- a/source/lib.js
+++ b/source/lib.js
@@ -469,6 +469,18 @@ function expressionizeIteration(exp) {
   )
 }
 
+/**
+* binops is an array of [__, op, __, exp] tuples
+* first is an expression
+*/
+function processLowBinaryOpExpression([first, binops]) {
+  const out = [makeLeftHandSideExpression(first)]
+  binops.forEach(([pre, op, post, exp]) => {
+    out.push(pre, op, post, makeLeftHandSideExpression(exp))
+  })
+  return out
+}
+
 function processBinaryOpExpression($0) {
   const expandedOps = expandChainedComparisons($0)
 
@@ -1410,6 +1422,10 @@ function makeLeftHandSideExpression(expression) {
     case "CallExpression":
     case "MemberExpression":
     case "ParenthesizedExpression":
+    case "DebuggerExpression": // wrapIIFE
+    case "SwitchExpression": // wrapIIFE
+    case "ThrowExpression": // wrapIIFE
+    case "TryExpression": // wrapIIFE
       return expression
     default:
       return {
@@ -2820,6 +2836,14 @@ function processReturnValue(func) {
   return true
 }
 
+function processLowUnaryExpression(pre, exp) {
+  if (!pre.length) return exp
+  return {
+    type: "UnaryExpression",
+    children: [...pre, makeLeftHandSideExpression(exp)],
+  }
+}
+
 function processUnaryExpression(pre, exp, post) {
   if (!(pre.length || post)) return exp
   // Handle "?" postfix
@@ -3154,6 +3178,8 @@ module.exports = {
   processCoffeeInterpolation,
   processConstAssignmentDeclaration,
   processLetAssignmentDeclaration,
+  processLowBinaryOpExpression,
+  processLowUnaryExpression,
   processParams,
   processProgram,
   processReturnValue,
diff --git a/source/main.coffee b/source/main.coffee
index e2c419ab2..c1a33887e 100644
--- a/source/main.coffee
+++ b/source/main.coffee
@@ -76,6 +76,10 @@ uncacheable = new Set [
   "JSXOptionalClosingFragment"
   "JSXTag"
   "LeftHandSideExpression"
+  "LowBinaryOpExpression"
+  "LowBinaryOpRHS"
+  "LowRHS"
+  "LowUnaryExpression"
   "MemberExpression"
   "MemberExpressionRest"
   "Nested"
@@ -126,6 +130,7 @@ uncacheable = new Set [
   "SingleLineAssignmentExpression"
   "SingleLineBinaryOpRHS"
   "SingleLineComment"
+  "SingleLineLowBinaryOpRHS"
   "SingleLineStatements"
   "SnugNamedProperty"
   "Statement"
diff --git a/source/parser.hera b/source/parser.hera
index df81a99af..81437775c 100644
--- a/source/parser.hera
+++ b/source/parser.hera
@@ -34,6 +34,8 @@ const {
   processCoffeeInterpolation,
   processConstAssignmentDeclaration,
   processLetAssignmentDeclaration,
+  processLowBinaryOpExpression,
+  processLowUnaryExpression,
   processProgram,
   processUnaryExpression,
   quoteString,
@@ -259,10 +261,31 @@ NonPipelineArgumentPart
     }
     return $1
 
+# NOTE: Match low-precedence binary ops first
+LowBinaryOpExpression
+  LowUnaryExpression LowBinaryOpRHS* ->
+    if (!$2.length) return $1
+    return processLowBinaryOpExpression($0)
+
+# NOTE: Excluding low-precedence binary ops
 BinaryOpExpression
   UnaryExpression BinaryOpRHS* ->
-    if ($2.length) return processBinaryOpExpression($0)
-    return $1
+    if (!$2.length) return $1
+    return processBinaryOpExpression($0)
+
+LowBinaryOpRHS
+  # Snug binary ops a+b
+  LowBinaryOp:op LowRHS:rhs ->
+    // Insert empty whitespace placeholder to maintan structure
+    return [[], op, [], rhs]
+  # Spaced binary ops a + b
+  # a
+  # + b
+  # Does not match
+  # a
+  # +b
+  NewlineBinaryOpAllowed ( NotDedented LowBinaryOp ( _ / ( EOS __ ) ) LowRHS ):rhs -> rhs
+  !NewlineBinaryOpAllowed SingleLineLowBinaryOpRHS -> $2
 
 BinaryOpRHS
   # Snug binary ops a+b
@@ -278,12 +301,23 @@ BinaryOpRHS
   NewlineBinaryOpAllowed ( NotDedented BinaryOp ( _ / ( EOS __ ) ) RHS ):rhs -> rhs
   !NewlineBinaryOpAllowed SingleLineBinaryOpRHS -> $2
 
+SingleLineLowBinaryOpRHS
+  # NOTE: It's named single line but that's only for the operator, the RHS can be after a newline
+  # This is to maintain compatibility with CoffeeScript conditions
+  _?:ws1 LowBinaryOp:op ( _ / ( EOS __ ) ):ws2 RHS:rhs ->
+    return [ws1 || [], op, ws2, rhs]
+
 SingleLineBinaryOpRHS
   # NOTE: It's named single line but that's only for the operator, the RHS can be after a newline
   # This is to maintain compatibility with CoffeeScript conditions
   _?:ws1 BinaryOp:op ( _ / ( EOS __ ) ):ws2 RHS:rhs ->
     return [ws1 || [], op, ws2, rhs]
 
+LowRHS
+  ParenthesizedAssignment
+  LowUnaryExpression
+  ExpressionizedStatement
+
 RHS
   ParenthesizedAssignment
   UnaryExpression
@@ -292,7 +326,13 @@ RHS
 ParenthesizedAssignment
   InsertOpenParen ActualAssignment InsertCloseParen
 
+LowUnaryExpression
+  # NOTE: Here is the transition from low precedence to high precedence
+  LowUnaryOp*:pre BinaryOpExpression:exp ->
+    return processLowUnaryExpression(pre, exp)
+
 # https://262.ecma-international.org/#prod-UnaryExpression
+# but excluding low-precedence unary ops
 UnaryExpression
   # NOTE: Merged AwaitExpression with UnaryOp
   # https://262.ecma-international.org/#prod-AwaitExpression
@@ -465,7 +505,7 @@ NestedTernaryRest
 # https://262.ecma-international.org/#prod-ShortCircuitExpression
 ShortCircuitExpression
   # NOTE: We don't need to track the precedence of all the binary operators so they all collapse into this
-  BinaryOpExpression
+  LowBinaryOpExpression
 
 PipelineExpression
   _?:ws PipelineHeadItem:head ( NotDedented Pipe __ PipelineTailItem )+:body ->
@@ -2597,6 +2637,10 @@ CoffeeWordAssignmentOp
   "and=" -> "&&="
   "or=" -> "||="
 
+LowBinaryOp
+  !CoffeeAndOrEnabled "and" NonIdContinue -> "&&"
+  !CoffeeAndOrEnabled "or" NonIdContinue -> "||"
+
 BinaryOp
   BinaryOpSymbol ->
     if (typeof $1 === "string") return { $loc, token: $1 }
@@ -2670,10 +2714,10 @@ BinaryOpSymbol
   "==" ->
     if(module.config.coffeeEq) return "==="
     return $1
-  "and" NonIdContinue -> "&&"
+  CoffeeAndOrEnabled "and" NonIdContinue -> "&&"
   "&&"
   CoffeeOfEnabled "of" NonIdContinue -> "in"
-  "or" NonIdContinue -> "||"
+  CoffeeAndOrEnabled "or" NonIdContinue -> "||"
   "||"
   # NOTE: ^^ must be above ^
   "^^" / ( "xor" NonIdContinue ) ->
@@ -2775,6 +2819,9 @@ Xor
 Xnor
   /!\^\^?/ / "xnor"
 
+LowUnaryOp
+  !CoffeeNotEnabled Not
+
 UnaryOp
   # Lookahead to prevent unary operators from overriding update operators
   # ++/-- or block unary operator shorthand
@@ -2782,7 +2829,7 @@ UnaryOp
     return { $loc, token: $0 }
   AwaitOp
   ( Delete / Void / Typeof ) !":" _?
-  Not # only when CoffeeNotEnabled (see definition of `Not`)
+  CoffeeNotEnabled Not
 
 # https://github.com/tc39/proposal-await.ops
 AwaitOp
@@ -4756,8 +4803,7 @@ New
     return { $loc, token: $1 }
 
 Not
-  # Not keyword only active in compat mode
-  CoffeeNotEnabled "not" NonIdContinue " "? ->
+  "not" NonIdContinue " "? ->
     return { $loc, token: "!" }
 
 Of
@@ -6135,6 +6181,11 @@ InsertVar
   "" ->
     return { $loc, token: "var " }
 
+CoffeeAndOrEnabled
+  "" ->
+    if(module.config.coffeeAndOr) return
+    return $skip
+
 CoffeeBinaryExistentialEnabled
   "" ->
     if(module.config.coffeeBinaryExistential) return
@@ -6274,6 +6325,7 @@ Reset
     module.config = parse.config = {
       autoVar: false,
       autoLet: false,
+      coffeeAndOr: false,
       coffeeBinaryExistential: false,
       coffeeBooleans: false,
       coffeeClasses: false,
@@ -6417,11 +6469,20 @@ Reset
     // default to deno compatibility if running in deno
     module.config.deno = typeof Deno !== "undefined"
 
+    // coffeeAndOrNot shorthand for coffeeAndOr and coffeeNot
+    Object.defineProperty(module.config, "coffeeAndOrNot", {
+      set(b) {
+        module.config.coffeeAndOr = b
+        module.config.coffeeNot = b
+      }
+    })
+
     // Expand setting coffeeCompat to the individual options
     Object.defineProperty(module.config, "coffeeCompat", {
       set(b) {
         for (const option of [
           "autoVar",
+          "coffeeAndOr",
           "coffeeBinaryExistential",
           "coffeeBooleans",
           "coffeeClasses",