diff --git a/changelog_unreleased/javascript/18397.md b/changelog_unreleased/javascript/18397.md
index 0d8eb39e7..952bd7561 100644
--- a/changelog_unreleased/javascript/18397.md
+++ b/changelog_unreleased/javascript/18397.md
@@ -1,13 +1,58 @@
-#### Avoid double parentheses around logical expression (#18397 by @fisker)
+#### Improve logical not expression print (#18397, #18401 by @fisker)
+
+- Fixed inner logical expression can be double parenthesized in some case.
+- Inline the expression in `if`/`while`/`do..while` condition, to reduce diff when changing condition to negated value.
 
 <!-- prettier-ignore -->
 ```jsx
 // Input
-const a = !(x || y /* foo */);
+if (!(
+  // `import("foo")`
+  node.type === "ImportExpression" ||
+  // `type foo = import("foo")`
+  node.type === "TSImportType"
+)) {
+} else if (
+  // `import("foo")`
+  node.type === "ImportExpression" ||
+  // `type foo = import("foo")`
+  node.type === "TSImportType" 
+) {
+}
 
 // Prettier stable
-const a = !((x || y) /* foo */);
+if (
+  !(
+    // `import("foo")`
+    (
+      node.type === "ImportExpression" ||
+      // `type foo = import("foo")`
+      node.type === "TSImportType"
+    )
+  )
+) {
+} else if (
+  // `import("foo")`
+  node.type === "ImportExpression" ||
+  // `type foo = import("foo")`
+  node.type === "TSImportType"
+) {
+}
 
 // Prettier main
-const a = !(x || y /* foo */);
+if (!(
+  // `import("foo")`
+  node.type === "ImportExpression" ||
+  // `type foo = import("foo")`
+  node.type === "TSImportType"
+)) {
+} else if (
+  // `import("foo")`
+  node.type === "ImportExpression" ||
+  // `type foo = import("foo")`
+  node.type === "TSImportType"
+) {
+}
 ```
+
+_This code example above is [a real world case](https://github.com/prettier/prettier/blob/edb53db4b1ec326d3f0f4fb683f56c83beefeba4/src/language-js/print/call-expression.js#L135-L155) right here in the Prettier codebase_
diff --git a/src/language-js/print/array.js b/src/language-js/print/array.js
index 9da195471..83653c854 100644
--- a/src/language-js/print/array.js
+++ b/src/language-js/print/array.js
@@ -22,7 +22,7 @@ import {
   isSignedNumericLiteral,
   shouldPrintComma,
 } from "../utilities/index.js";
-import { printOptionalToken } from "./misc.js";
+import { printOptionalToken } from "./miscellaneous.js";
 import { printTypeAnnotationProperty } from "./type-annotation.js";
 
 /** @import {Doc} from "../../document/index.js" */
diff --git a/src/language-js/print/binaryish.js b/src/language-js/print/binaryish.js
index bd99a1fc5..e1673f630 100644
--- a/src/language-js/print/binaryish.js
+++ b/src/language-js/print/binaryish.js
@@ -20,6 +20,7 @@ import {
   hasLeadingOwnLineComment,
   isArrayExpression,
   isBinaryish,
+  isBooleanTypeCoercion,
   isCallExpression,
   isJsxElement,
   isMemberExpression,
@@ -114,7 +115,7 @@ function printBinaryishExpression(path, options, print) {
       grandparent.type !== "NewExpression") ||
     parent.type === "TemplateLiteral" ||
     (key === "argument" && parent.type === "UnaryExpression") ||
-    isBooleanTypeCoercion(path);
+    (key === "arguments" && isBooleanTypeCoercion(parent));
 
   const shouldIndentIfInlining =
     parent.type === "AssignmentExpression" ||
@@ -395,27 +396,4 @@ function isVueFilterSequenceExpression(path, options) {
   );
 }
 
-/**
-@returns {boolean}
-*/
-function isBooleanTypeCoercion(path) {
-  if (path.key !== "arguments") {
-    return false;
-  }
-
-  const { parent } = path;
-  if (
-    !(
-      isCallExpression(parent) &&
-      !parent.optional &&
-      parent.arguments.length === 1
-    )
-  ) {
-    return false;
-  }
-
-  const { callee } = parent;
-  return callee.type === "Identifier" && callee.name === "Boolean";
-}
-
 export { printBinaryishExpression, shouldInlineLogicalExpression };
diff --git a/src/language-js/print/call-expression.js b/src/language-js/print/call-expression.js
index 7e3034d67..d199510e5 100644
--- a/src/language-js/print/call-expression.js
+++ b/src/language-js/print/call-expression.js
@@ -13,7 +13,7 @@ import {
 } from "../utilities/index.js";
 import printCallArguments from "./call-arguments.js";
 import printMemberChain from "./member-chain.js";
-import { printOptionalToken } from "./misc.js";
+import { printOptionalToken } from "./miscellaneous.js";
 
 /*
 - `NewExpression`
diff --git a/src/language-js/print/class.js b/src/language-js/print/class.js
index db49d5650..94253721a 100644
--- a/src/language-js/print/class.js
+++ b/src/language-js/print/class.js
@@ -29,7 +29,7 @@ import {
   printDefiniteToken,
   printOptionalToken,
   printTypeScriptAccessibilityToken,
-} from "./misc.js";
+} from "./miscellaneous.js";
 import { printPropertyKey } from "./property.js";
 import { printTypeAnnotationProperty } from "./type-annotation.js";
 
diff --git a/src/language-js/print/component.js b/src/language-js/print/component.js
index e5f2040c3..0c9c7178d 100644
--- a/src/language-js/print/component.js
+++ b/src/language-js/print/component.js
@@ -10,7 +10,7 @@ import { printDanglingComments } from "../../main/comments/print.js";
 import getNextNonSpaceNonCommentCharacter from "../../utilities/get-next-non-space-non-comment-character.js";
 import { locEnd } from "../loc.js";
 import { isNextLineEmpty, shouldPrintComma } from "../utilities/index.js";
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 
 /**
  * @import AstPath from "../../common/ast-path.js"
diff --git a/src/language-js/print/enum.js b/src/language-js/print/enum.js
index 0df9fbbe7..10a6ff65d 100644
--- a/src/language-js/print/enum.js
+++ b/src/language-js/print/enum.js
@@ -1,4 +1,4 @@
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 import { printObject as printEnumMembers } from "./object.js";
 
 /*
diff --git a/src/language-js/print/estree.js b/src/language-js/print/estree.js
index 6a9bbb0f3..e93e7a102 100644
--- a/src/language-js/print/estree.js
+++ b/src/language-js/print/estree.js
@@ -49,7 +49,7 @@ import {
   adjustClause,
   printDefiniteToken,
   printOptionalToken,
-} from "./misc.js";
+} from "./miscellaneous.js";
 import {
   printExportDeclaration,
   printImportDeclaration,
diff --git a/src/language-js/print/flow.js b/src/language-js/print/flow.js
index 24230abfb..044756d68 100644
--- a/src/language-js/print/flow.js
+++ b/src/language-js/print/flow.js
@@ -37,7 +37,7 @@ import { printIntersectionType } from "./intersection-type.js";
 import { printBigInt } from "./literal.js";
 import { printFlowMappedTypeProperty } from "./mapped-type.js";
 import { printMatch, printMatchCase, printMatchPattern } from "./match.js";
-import { printDeclareToken, printOptionalToken } from "./misc.js";
+import { printDeclareToken, printOptionalToken } from "./miscellaneous.js";
 import { printExportDeclaration } from "./module.js";
 import { printOpaqueType } from "./opaque-type.js";
 import { printPropertyKey } from "./property.js";
diff --git a/src/language-js/print/for-statement.js b/src/language-js/print/for-statement.js
index e0a474747..7f3e07fa1 100644
--- a/src/language-js/print/for-statement.js
+++ b/src/language-js/print/for-statement.js
@@ -6,7 +6,7 @@ import {
   softline,
 } from "../../document/index.js";
 import { printDanglingComments } from "../../main/comments/print.js";
-import { adjustClause } from "./misc.js";
+import { adjustClause } from "./miscellaneous.js";
 
 function printForStatement(path, options, print) {
   const { node } = path;
diff --git a/src/language-js/print/function-type.js b/src/language-js/print/function-type.js
index 5f1e094c8..b9d698904 100644
--- a/src/language-js/print/function-type.js
+++ b/src/language-js/print/function-type.js
@@ -6,7 +6,7 @@ import {
   printFunctionParameters,
   shouldGroupFunctionParameters,
 } from "./function-parameters.js";
-import { printAbstractToken } from "./misc.js";
+import { printAbstractToken } from "./miscellaneous.js";
 import { printTypeAnnotationProperty } from "./type-annotation.js";
 
 /**
diff --git a/src/language-js/print/function.js b/src/language-js/print/function.js
index c0cc75b37..1d67d14cc 100644
--- a/src/language-js/print/function.js
+++ b/src/language-js/print/function.js
@@ -27,7 +27,7 @@ import {
   shouldBreakFunctionParameters,
   shouldGroupFunctionParameters,
 } from "./function-parameters.js";
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 import { printPropertyKey } from "./property.js";
 import { printTypeAnnotationProperty } from "./type-annotation.js";
 
diff --git a/src/language-js/print/hook.js b/src/language-js/print/hook.js
index c1bf34283..e37225f75 100644
--- a/src/language-js/print/hook.js
+++ b/src/language-js/print/hook.js
@@ -4,7 +4,7 @@ import {
   printFunctionParameters,
   shouldGroupFunctionParameters,
 } from "./function-parameters.js";
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 
 /**
  * @import AstPath from "../../common/ast-path.js"
diff --git a/src/language-js/print/if-statement.js b/src/language-js/print/if-statement.js
index 87c282333..9f04b1859 100644
--- a/src/language-js/print/if-statement.js
+++ b/src/language-js/print/if-statement.js
@@ -1,11 +1,11 @@
-import { group, hardline, indent, softline } from "../../document/index.js";
+import { group, hardline } from "../../document/index.js";
 import { printDanglingComments } from "../../main/comments/print.js";
 import {
   CommentCheckFlags,
   hasComment,
   needsHardlineAfterDanglingComment,
 } from "../utilities/index.js";
-import { adjustClause } from "./misc.js";
+import { adjustClause, printIfStatementCondition } from "./miscellaneous.js";
 
 /**
  * @import AstPath from "../../common/ast-path.js"
@@ -17,7 +17,7 @@ function printIfStatement(path, options, print) {
   const consequent = adjustClause(node.consequent, print("consequent"));
   const opening = group([
     "if (",
-    group([indent([softline, print("test")]), softline]),
+    printIfStatementCondition(path, options, print),
     ")",
     consequent,
   ]);
diff --git a/src/language-js/print/indexed-access-type.js b/src/language-js/print/indexed-access-type.js
index f5037daea..fdc96f750 100644
--- a/src/language-js/print/indexed-access-type.js
+++ b/src/language-js/print/indexed-access-type.js
@@ -1,4 +1,4 @@
-import { printOptionalToken } from "./misc.js";
+import { printOptionalToken } from "./miscellaneous.js";
 
 /*
 - `TSIndexedAccessType`(TypeScript)
diff --git a/src/language-js/print/member-chain.js b/src/language-js/print/member-chain.js
index 46dbc3fd4..41a7311ad 100644
--- a/src/language-js/print/member-chain.js
+++ b/src/language-js/print/member-chain.js
@@ -28,7 +28,7 @@ import {
 import { printBindExpressionCallee } from "./bind-expression.js";
 import printCallArguments from "./call-arguments.js";
 import { printMemberLookup } from "./member.js";
-import { printOptionalToken } from "./misc.js";
+import { printOptionalToken } from "./miscellaneous.js";
 
 /**
  * @import {Doc} from "../../document/index.js"
diff --git a/src/language-js/print/member.js b/src/language-js/print/member.js
index 3fbcfa3c0..45773b085 100644
--- a/src/language-js/print/member.js
+++ b/src/language-js/print/member.js
@@ -5,7 +5,7 @@ import {
   isMemberExpression,
   isNumericLiteral,
 } from "../utilities/index.js";
-import { printOptionalToken } from "./misc.js";
+import { printOptionalToken } from "./miscellaneous.js";
 
 const isCallExpressionWithArguments = (node) => {
   if (node.type === "ChainExpression" || node.type === "TSNonNullExpression") {
diff --git a/src/language-js/print/method-signature.js b/src/language-js/print/method-signature.js
index 3db90cb70..2fe02d3db 100644
--- a/src/language-js/print/method-signature.js
+++ b/src/language-js/print/method-signature.js
@@ -7,7 +7,7 @@ import {
 import {
   printOptionalToken,
   printTypeScriptAccessibilityToken,
-} from "./misc.js";
+} from "./miscellaneous.js";
 import { printTypeAnnotationProperty } from "./type-annotation.js";
 
 function printMethodSignature(path, options, print) {
diff --git a/src/language-js/print/misc.js b/src/language-js/print/miscellaneous.js
similarity index 67%
rename from src/language-js/print/misc.js
rename to src/language-js/print/miscellaneous.js
index d3635dbc4..a6a78174f 100644
--- a/src/language-js/print/misc.js
+++ b/src/language-js/print/miscellaneous.js
@@ -1,4 +1,4 @@
-import { indent, line } from "../../document/index.js";
+import { group, indent, line, softline } from "../../document/index.js";
 import {
   CommentCheckFlags,
   createTypeCheckFunction,
@@ -113,11 +113,65 @@ function printTypeScriptAccessibilityToken(node) {
   return node.accessibility ? node.accessibility + " " : "";
 }
 
+const isLogicalNot = (node) =>
+  node.type === "UnaryExpression" && node.operator === "!";
+
+function shouldInlineCondition(node) {
+  if (hasComment(node)) {
+    return false;
+  }
+
+  /*
+  Main purpose here is to avoid indent level change when switching to negative condition
+
+  The following case:
+
+  ```js
+  if (!foo({
+    bar
+  }));
+  ```
+
+  does look nice, but once `!` is removed, it's hard to known how the `CallExpression` will print
+
+  ```js
+  if (foo({
+    bar
+  }));
+  ```
+
+  so we are not going to inline it.
+  */
+
+  // `!(a | b)` and `!!(a | b)`, but not `!!!(a | b)`
+  if (!isLogicalNot(node)) {
+    return false;
+  }
+
+  node = node.argument;
+  node = isLogicalNot(node) ? node.argument : node;
+
+  return node.type === "LogicalExpression";
+}
+
+function printIfOrWhileCondition(path, options, print) {
+  const conditionDoc = print("test");
+
+  if (shouldInlineCondition(path.node.test)) {
+    return conditionDoc;
+  }
+
+  return group([indent([softline, conditionDoc]), softline]);
+}
+
 export {
   adjustClause,
   printAbstractToken,
   printDeclareToken,
   printDefiniteToken,
+  printIfOrWhileCondition as printDoWhileStatementCondition,
+  printIfOrWhileCondition as printIfStatementCondition,
   printOptionalToken,
   printTypeScriptAccessibilityToken,
+  printIfOrWhileCondition as printWhileStatementCondition,
 };
diff --git a/src/language-js/print/module-declaration.js b/src/language-js/print/module-declaration.js
index 3ad87fc27..1a7b4d4b0 100644
--- a/src/language-js/print/module-declaration.js
+++ b/src/language-js/print/module-declaration.js
@@ -1,5 +1,5 @@
 import { group } from "../../document/index.js";
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 
 function printModuleDeclaration(path, options, print) {
   const { node } = path;
diff --git a/src/language-js/print/module.js b/src/language-js/print/module.js
index ee4dbc6e7..9e4a0cda5 100644
--- a/src/language-js/print/module.js
+++ b/src/language-js/print/module.js
@@ -23,7 +23,7 @@ import {
   shouldPrintComma,
 } from "../utilities/index.js";
 import { printDecoratorsBeforeExport } from "./decorators.js";
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 import { printObject } from "./object.js";
 
 /**
diff --git a/src/language-js/print/object.js b/src/language-js/print/object.js
index 38ca29de2..ce93bca21 100644
--- a/src/language-js/print/object.js
+++ b/src/language-js/print/object.js
@@ -23,7 +23,7 @@ import {
   shouldPrintComma,
 } from "../utilities/index.js";
 import { shouldHugTheOnlyParameter } from "./function-parameters.js";
-import { printOptionalToken } from "./misc.js";
+import { printOptionalToken } from "./miscellaneous.js";
 import { printTypeAnnotationProperty } from "./type-annotation.js";
 
 /** @import {Doc} from "../../document/index.js" */
diff --git a/src/language-js/print/opaque-type.js b/src/language-js/print/opaque-type.js
index 1a756447a..d6d65e794 100644
--- a/src/language-js/print/opaque-type.js
+++ b/src/language-js/print/opaque-type.js
@@ -1,5 +1,5 @@
 import { group, indent, line } from "../../document/index.js";
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 
 /*
 - `DeclareOpaqueType`(flow)
diff --git a/src/language-js/print/type-alias.js b/src/language-js/print/type-alias.js
index 0ecdfbd36..01f26809e 100644
--- a/src/language-js/print/type-alias.js
+++ b/src/language-js/print/type-alias.js
@@ -1,5 +1,5 @@
 import { printAssignment } from "./assignment.js";
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 
 /*
 - `DeclareTypeAlias`(flow)
diff --git a/src/language-js/print/typescript.js b/src/language-js/print/typescript.js
index b1135d2f8..8fdf294fb 100644
--- a/src/language-js/print/typescript.js
+++ b/src/language-js/print/typescript.js
@@ -29,7 +29,7 @@ import { printMethodSignature } from "./method-signature.js";
 import {
   printOptionalToken,
   printTypeScriptAccessibilityToken,
-} from "./misc.js";
+} from "./miscellaneous.js";
 import { printImportKind } from "./module.js";
 import { printModuleDeclaration } from "./module-declaration.js";
 import { printPropertyKey } from "./property.js";
diff --git a/src/language-js/print/variable-declaration.js b/src/language-js/print/variable-declaration.js
index aa58642bc..71978af8e 100644
--- a/src/language-js/print/variable-declaration.js
+++ b/src/language-js/print/variable-declaration.js
@@ -1,6 +1,6 @@
 import { group, hardline, indent, line } from "../../document/index.js";
 import { hasComment } from "../utilities/index.js";
-import { printDeclareToken } from "./misc.js";
+import { printDeclareToken } from "./miscellaneous.js";
 
 function printVariableDeclaration(path, options, print) {
   const { node } = path;
diff --git a/src/language-js/print/while-statement.js b/src/language-js/print/while-statement.js
index a5d3a9fdb..cb7888876 100644
--- a/src/language-js/print/while-statement.js
+++ b/src/language-js/print/while-statement.js
@@ -1,10 +1,14 @@
-import { group, hardline, indent, softline } from "../../document/index.js";
-import { adjustClause } from "./misc.js";
+import { group, hardline } from "../../document/index.js";
+import {
+  adjustClause,
+  printDoWhileStatementCondition,
+  printWhileStatementCondition,
+} from "./miscellaneous.js";
 
 function printWhileStatement(path, options, print) {
   return group([
     "while (",
-    group([indent([softline, print("test")]), softline]),
+    printWhileStatementCondition(path, options, print),
     ")",
     adjustClause(path.node.body, print("body")),
   ]);
@@ -19,7 +23,7 @@ function printDoWhileStatement(path, options, print) {
     doBody,
     body.type === "BlockStatement" ? " " : hardline,
     "while (",
-    group([indent([softline, print("test")]), softline]),
+    printDoWhileStatementCondition(path, options, print),
     ")",
     options.semi ? ";" : "",
   ];
diff --git a/src/language-js/utilities/index.js b/src/language-js/utilities/index.js
index 386bd4466..6800d93b4 100644
--- a/src/language-js/utilities/index.js
+++ b/src/language-js/utilities/index.js
@@ -1098,6 +1098,19 @@ function shouldUnionTypePrintOwnComments({ key, parent }) {
   return true;
 }
 
+/**
+@returns {boolean}
+*/
+function isBooleanTypeCoercion(node) {
+  return (
+    node.type === "CallExpression" &&
+    !node.optional &&
+    node.arguments.length === 1 &&
+    node.callee.type === "Identifier" &&
+    node.callee.name === "Boolean"
+  );
+}
+
 export {
   CommentCheckFlags,
   createTypeCheckFunction,
@@ -1119,6 +1132,7 @@ export {
   isBinaryish,
   isBitwiseOperator,
   isBooleanLiteral,
+  isBooleanTypeCoercion,
   isCallExpression,
   isCallLikeExpression,
   isConditionalType,
diff --git a/tests/format/js/if/condition-break/__snapshots__/format.test.js.snap b/tests/format/js/if/condition-break/__snapshots__/format.test.js.snap
new file mode 100644
index 000000000..e638459b3
--- /dev/null
+++ b/tests/format/js/if/condition-break/__snapshots__/format.test.js.snap
@@ -0,0 +1,450 @@
+// Jest Snapshot v1, https://jestjs.io/docs/snapshot-testing
+
+exports[`boolean-expression.js format 1`] = `
+====================================options=====================================
+parsers: ["babel", "flow", "typescript"]
+printWidth: 80
+                                                                                | printWidth
+=====================================input======================================
+if (Boolean(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+while (Boolean(
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference"));
+
+do {} while (Boolean(
+  node.type === "ImportExpression" ??
+  node.type === "TSImportType" ??
+  node.type === "TSExternalModuleReference"));
+
+if (!!!Boolean(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (!Boolean(!!Boolean(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")));
+
+if ( // comment
+Boolean(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (Boolean // comment
+(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (Boolean?.
+(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+
+=====================================output=====================================
+if (
+  Boolean(
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference",
+  )
+);
+
+while (
+  Boolean(
+    node.type === "ImportExpression" &&
+    node.type === "TSImportType" &&
+    node.type === "TSExternalModuleReference",
+  )
+);
+
+do {} while (
+  Boolean(
+    node.type === "ImportExpression" ??
+    node.type === "TSImportType" ??
+    node.type === "TSExternalModuleReference",
+  )
+);
+
+if (
+  !!!Boolean(
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference",
+  )
+);
+
+if (
+  !Boolean(
+    !!Boolean(
+      node.type === "ImportExpression" ||
+      node.type === "TSImportType" ||
+      node.type === "TSExternalModuleReference",
+    ),
+  )
+);
+
+if (
+  // comment
+  Boolean(
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference",
+  )
+);
+
+if (
+  Boolean(
+    // comment
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference",
+  )
+);
+
+if (
+  Boolean?.(
+    node.type === "ImportExpression" ||
+      node.type === "TSImportType" ||
+      node.type === "TSExternalModuleReference",
+  )
+);
+
+================================================================================
+`;
+
+exports[`real-world-cases.js format 1`] = `
+====================================options=====================================
+parsers: ["babel", "flow", "typescript"]
+printWidth: 80
+                                                                                | printWidth
+=====================================input======================================
+{{
+if (!doesImmediatelyReturnFunctionExpression({ node: current,returns,})) {
+      }
+if (!validatePredefinedFormat(config, name, node, originalName, modifiers)) {}
+}}
+if (
+        ![
+          AST_NODE_TYPES.ArrowFunctionExpression,
+          AST_NODE_TYPES.FunctionDeclaration,
+          AST_NODE_TYPES.FunctionExpression,
+        ].includes(blockParent.type)
+      );
+  if (
+          !allowInGenericTypeArguments
+            .map(s => s.replaceAll(' ', ''))
+            .includes(fullyQualifiedName)
+        ) {}
+
+if(foo) {
+//
+}else if (
+        !(i === 0 ? validFirstIdentCharRE : validIdentCharRE).test(char)
+      ) {}
+if (!processDefineProps(
+    ctx,
+    node.arguments[0],
+    declId,
+    true /* isWithDefaults */,
+  )) {}
+if (processDefineProps(
+    ctx,
+    node.arguments[0],
+    declId,
+    true /* isWithDefaults */,
+  )) {}
+
+=====================================output=====================================
+{
+  {
+    if (!doesImmediatelyReturnFunctionExpression({ node: current, returns })) {
+    }
+    if (
+      !validatePredefinedFormat(config, name, node, originalName, modifiers)
+    ) {
+    }
+  }
+}
+if (
+  ![
+    AST_NODE_TYPES.ArrowFunctionExpression,
+    AST_NODE_TYPES.FunctionDeclaration,
+    AST_NODE_TYPES.FunctionExpression,
+  ].includes(blockParent.type)
+);
+if (
+  !allowInGenericTypeArguments
+    .map((s) => s.replaceAll(" ", ""))
+    .includes(fullyQualifiedName)
+) {
+}
+
+if (foo) {
+  //
+} else if (!(i === 0 ? validFirstIdentCharRE : validIdentCharRE).test(char)) {
+}
+if (
+  !processDefineProps(ctx, node.arguments[0], declId, true /* isWithDefaults */)
+) {
+}
+if (
+  processDefineProps(ctx, node.arguments[0], declId, true /* isWithDefaults */)
+) {
+}
+
+================================================================================
+`;
+
+exports[`unary-expression.js format 1`] = `
+====================================options=====================================
+parsers: ["babel", "flow", "typescript"]
+printWidth: 80
+                                                                                | printWidth
+=====================================input======================================
+if (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+while (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+do {} while (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+
+if (!!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if(typeof (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+
+if ( // comment
+!!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (! // comment
+!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (!! // comment
+(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if(1){
+//
+}else {if(! (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) do {
+//
+} while (! (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) else if (! (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) while (! (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) {
+//
+}}
+if(2){
+//
+}else {if( (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) do {
+//
+} while ( (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) else if ( (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) while ( (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) {
+//
+}}
+
+if ((
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference") || !(
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference")) {}else if (!(
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference") || (
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference")){}
+
+=====================================output=====================================
+if (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"
+));
+
+while (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"
+));
+
+do {} while (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"
+));
+
+if (!!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"
+));
+
+if (
+  typeof (
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference"
+  )
+);
+
+if (
+  // comment
+  !!(
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference"
+  )
+);
+
+if (!(
+  // comment
+  !(
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference"
+  )
+));
+
+if (!!(
+  // comment
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"
+));
+
+if (1) {
+  //
+} else {
+  if (!(
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference"
+  ))
+    do {
+      //
+    } while (!(
+      node.type === "ImportExpression" ||
+      node.type === "TSImportType" ||
+      node.type === "TSExternalModuleReference"
+    ));
+  else if (!(
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference"
+  ))
+    while (!(
+      node.type === "ImportExpression" ||
+      node.type === "TSImportType" ||
+      node.type === "TSExternalModuleReference"
+    )) {
+      //
+    }
+}
+if (2) {
+  //
+} else {
+  if (
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference"
+  )
+    do {
+      //
+    } while (
+      node.type === "ImportExpression" ||
+      node.type === "TSImportType" ||
+      node.type === "TSExternalModuleReference"
+    );
+  else if (
+    node.type === "ImportExpression" ||
+    node.type === "TSImportType" ||
+    node.type === "TSExternalModuleReference"
+  )
+    while (
+      node.type === "ImportExpression" ||
+      node.type === "TSImportType" ||
+      node.type === "TSExternalModuleReference"
+    ) {
+      //
+    }
+}
+
+if (
+  (node.type === "ImportExpression" &&
+    node.type === "TSImportType" &&
+    node.type === "TSExternalModuleReference") ||
+  !(
+    node.type === "ImportExpression" &&
+    node.type === "TSImportType" &&
+    node.type === "TSExternalModuleReference"
+  )
+) {
+} else if (
+  !(
+    node.type === "ImportExpression" &&
+    node.type === "TSImportType" &&
+    node.type === "TSExternalModuleReference"
+  ) ||
+  (node.type === "ImportExpression" &&
+    node.type === "TSImportType" &&
+    node.type === "TSExternalModuleReference")
+) {
+}
+
+================================================================================
+`;
diff --git a/tests/format/js/if/condition-break/boolean-expression.js b/tests/format/js/if/condition-break/boolean-expression.js
new file mode 100644
index 000000000..f19f15887
--- /dev/null
+++ b/tests/format/js/if/condition-break/boolean-expression.js
@@ -0,0 +1,43 @@
+if (Boolean(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+while (Boolean(
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference"));
+
+do {} while (Boolean(
+  node.type === "ImportExpression" ??
+  node.type === "TSImportType" ??
+  node.type === "TSExternalModuleReference"));
+
+if (!!!Boolean(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (!Boolean(!!Boolean(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")));
+
+if ( // comment
+Boolean(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (Boolean // comment
+(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (Boolean?.
+(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
diff --git a/tests/format/js/if/condition-break/format.test.js b/tests/format/js/if/condition-break/format.test.js
new file mode 100644
index 000000000..67c251cce
--- /dev/null
+++ b/tests/format/js/if/condition-break/format.test.js
@@ -0,0 +1 @@
+runFormatTest(import.meta, ["babel", "flow", "typescript"]);
diff --git a/tests/format/js/if/condition-break/real-world-cases.js b/tests/format/js/if/condition-break/real-world-cases.js
new file mode 100644
index 000000000..ecc0b355d
--- /dev/null
+++ b/tests/format/js/if/condition-break/real-world-cases.js
@@ -0,0 +1,35 @@
+{{
+if (!doesImmediatelyReturnFunctionExpression({ node: current,returns,})) {
+      }
+if (!validatePredefinedFormat(config, name, node, originalName, modifiers)) {}
+}}
+if (
+        ![
+          AST_NODE_TYPES.ArrowFunctionExpression,
+          AST_NODE_TYPES.FunctionDeclaration,
+          AST_NODE_TYPES.FunctionExpression,
+        ].includes(blockParent.type)
+      );
+  if (
+          !allowInGenericTypeArguments
+            .map(s => s.replaceAll(' ', ''))
+            .includes(fullyQualifiedName)
+        ) {}
+
+if(foo) {
+//
+}else if (
+        !(i === 0 ? validFirstIdentCharRE : validIdentCharRE).test(char)
+      ) {}
+if (!processDefineProps(
+    ctx,
+    node.arguments[0],
+    declId,
+    true /* isWithDefaults */,
+  )) {}
+if (processDefineProps(
+    ctx,
+    node.arguments[0],
+    declId,
+    true /* isWithDefaults */,
+  )) {}
diff --git a/tests/format/js/if/condition-break/unary-expression.js b/tests/format/js/if/condition-break/unary-expression.js
new file mode 100644
index 000000000..ca6b18d74
--- /dev/null
+++ b/tests/format/js/if/condition-break/unary-expression.js
@@ -0,0 +1,97 @@
+if (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+while (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+do {} while (!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+
+if (!!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if(typeof (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+
+if ( // comment
+!!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (! // comment
+!(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if (!! // comment
+(
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference"));
+
+if(1){
+//
+}else {if(! (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) do {
+//
+} while (! (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) else if (! (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) while (! (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) {
+//
+}}
+if(2){
+//
+}else {if( (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) do {
+//
+} while ( (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) else if ( (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) while ( (
+  node.type === "ImportExpression" ||
+  node.type === "TSImportType" ||
+  node.type === "TSExternalModuleReference")) {
+//
+}}
+
+if ((
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference") || !(
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference")) {}else if (!(
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference") || (
+  node.type === "ImportExpression" &&
+  node.type === "TSImportType" &&
+  node.type === "TSExternalModuleReference")){}
diff --git a/tests/format/js/logical-expressions/__snapshots__/format.test.js.snap b/tests/format/js/logical-expressions/__snapshots__/format.test.js.snap
index b7b2dad53..d7bd916c5 100644
--- a/tests/format/js/logical-expressions/__snapshots__/format.test.js.snap
+++ b/tests/format/js/logical-expressions/__snapshots__/format.test.js.snap
@@ -118,23 +118,21 @@ const foo = () =>
 ];
 
 // Realworld case from Prettier repo
-if (
-  !(
-    // \`import("foo")\`
-    node.type === "ImportExpression" ||
-    // \`type foo = import("foo")\`
-    node.type === "TSImportType" ||
-    // \`import type A = require("foo")\`
-    node.type === "TSExternalModuleReference" ||
-    // \`require("foo")\`
-    // \`require.resolve("foo")\`
-    // \`require.resolve.paths("foo")\`
-    // \`import.meta.resolve("foo")\`
-    (node.type === "CallExpression" &&
-      !node.optional &&
-      isNodeMatches(node.callee, moduleImportCallees))
-  )
-) {
+if (!(
+  // \`import("foo")\`
+  node.type === "ImportExpression" ||
+  // \`type foo = import("foo")\`
+  node.type === "TSImportType" ||
+  // \`import type A = require("foo")\`
+  node.type === "TSExternalModuleReference" ||
+  // \`require("foo")\`
+  // \`require.resolve("foo")\`
+  // \`require.resolve.paths("foo")\`
+  // \`import.meta.resolve("foo")\`
+  (node.type === "CallExpression" &&
+    !node.optional &&
+    isNodeMatches(node.callee, moduleImportCallees))
+)) {
 }
 
 // Realworld case from Babel repo