diff --git a/internal/js_ast/js_ast.go b/internal/js_ast/js_ast.go
index 725eabe9126..628e9aed64b 100644
--- a/internal/js_ast/js_ast.go
+++ b/internal/js_ast/js_ast.go
@@ -743,7 +743,7 @@ type EImportString struct {
 	// because esbuild is not Webpack. But we do preserve them since doing so is
 	// harmless, easy to maintain, and useful to people. See the Webpack docs for
 	// more info: https://webpack.js.org/api/module-methods/#magic-comments.
-	LeadingInteriorComments []Comment
+	WebpackComments []Comment
 
 	ImportRecordIndex uint32
 }
@@ -753,7 +753,7 @@ type EImportCall struct {
 	OptionsOrNil Expr
 
 	// See the comment for this same field on "EImportString" for more information
-	LeadingInteriorComments []Comment
+	WebpackComments []Comment
 }
 
 type Stmt struct {
diff --git a/internal/js_lexer/js_lexer.go b/internal/js_lexer/js_lexer.go
index 85c12cddc17..ebcdb672e14 100644
--- a/internal/js_lexer/js_lexer.go
+++ b/internal/js_lexer/js_lexer.go
@@ -245,7 +245,8 @@ type MaybeSubstring struct {
 }
 
 type Lexer struct {
-	CommentsToPreserveBefore     []js_ast.Comment
+	LegalCommentsBeforeToken     []js_ast.Comment
+	WebpackComments              *[]js_ast.Comment
 	AllOriginalComments          []logger.Range
 	Identifier                   MaybeSubstring
 	log                          logger.Log
@@ -288,7 +289,6 @@ type Lexer struct {
 	ts                              config.TSOptions
 	HasNewlineBefore                bool
 	HasPureCommentBefore            bool
-	PreserveAllCommentsBefore       bool
 	IsLegacyOctalLiteral            bool
 	PrevTokenWasAwaitKeyword        bool
 	rescanCloseBraceAsTemplateToken bool
@@ -1212,7 +1212,7 @@ func (lexer *Lexer) Next() {
 	lexer.HasNewlineBefore = lexer.end == 0
 	lexer.HasPureCommentBefore = false
 	lexer.PrevTokenWasAwaitKeyword = false
-	lexer.CommentsToPreserveBefore = nil
+	lexer.LegalCommentsBeforeToken = nil
 
 	for {
 		lexer.start = lexer.end
@@ -2746,10 +2746,19 @@ func scanForPragmaArg(kind pragmaArg, start int, pragma string, text string) (lo
 	}, true
 }
 
+func isUpperASCII(c byte) bool {
+	return c >= 'A' && c <= 'Z'
+}
+
+func isLetterASCII(c byte) bool {
+	return (c >= 'a' && c <= 'z') || (c >= 'A' && c <= 'Z')
+}
+
 func (lexer *Lexer) scanCommentText() {
 	text := lexer.source.Contents[lexer.start:lexer.end]
 	hasLegalAnnotation := len(text) > 2 && text[2] == '!'
 	isMultiLineComment := text[1] == '*'
+	isWebpackComment := false
 
 	// Save the original comment text so we can subtract comments from the
 	// character frequency analysis used by symbol minification
@@ -2800,15 +2809,43 @@ func (lexer *Lexer) scanCommentText() {
 					lexer.SourceMappingURL = arg
 				}
 			}
+
+		case 'w':
+			// Webpack magic comments use this regular expression: /(^|\W)webpack[A-Z]{1,}[A-Za-z]{1,}:/
+			if lexer.WebpackComments != nil && !isWebpackComment && strings.HasPrefix(text[i:], "webpack") && !isLetterASCII(text[i-1]) {
+				j := i + 7
+				upperCount := 0
+				for isUpperASCII(text[j]) {
+					upperCount++
+					j++
+				}
+				if upperCount > 0 {
+					letterCount := 0
+					for isLetterASCII(text[j]) {
+						letterCount++
+						j++
+					}
+					if letterCount > 0 && text[j] == ':' {
+						isWebpackComment = true
+					}
+				}
+			}
 		}
 	}
 
-	if hasLegalAnnotation || lexer.PreserveAllCommentsBefore {
-		if isMultiLineComment {
-			text = helpers.RemoveMultiLineCommentIndent(lexer.source.Contents[:lexer.start], text)
-		}
+	if isMultiLineComment && (hasLegalAnnotation || isWebpackComment) {
+		text = helpers.RemoveMultiLineCommentIndent(lexer.source.Contents[:lexer.start], text)
+	}
+
+	if hasLegalAnnotation {
+		lexer.LegalCommentsBeforeToken = append(lexer.LegalCommentsBeforeToken, js_ast.Comment{
+			Loc:  logger.Loc{Start: int32(lexer.start)},
+			Text: text,
+		})
+	}
 
-		lexer.CommentsToPreserveBefore = append(lexer.CommentsToPreserveBefore, js_ast.Comment{
+	if isWebpackComment {
+		*lexer.WebpackComments = append(*lexer.WebpackComments, js_ast.Comment{
 			Loc:  logger.Loc{Start: int32(lexer.start)},
 			Text: text,
 		})
diff --git a/internal/js_parser/js_parser.go b/internal/js_parser/js_parser.go
index 179d5b13a82..9a48489af21 100644
--- a/internal/js_parser/js_parser.go
+++ b/internal/js_parser/js_parser.go
@@ -3673,10 +3673,10 @@ func (p *parser) parseImportExpr(loc logger.Loc, level js_ast.L) js_ast.Expr {
 	oldAllowIn := p.allowIn
 	p.allowIn = true
 
-	p.lexer.PreserveAllCommentsBefore = true
+	var webpackComments []js_ast.Comment
+	oldWebpackComments := p.lexer.WebpackComments
+	p.lexer.WebpackComments = &webpackComments
 	p.lexer.Expect(js_lexer.TOpenParen)
-	comments := p.lexer.CommentsToPreserveBefore
-	p.lexer.PreserveAllCommentsBefore = false
 
 	value := p.parseExpr(js_ast.LComma)
 	var optionsOrNil js_ast.Expr
@@ -3696,13 +3696,14 @@ func (p *parser) parseImportExpr(loc logger.Loc, level js_ast.L) js_ast.Expr {
 		}
 	}
 
+	p.lexer.WebpackComments = oldWebpackComments
 	p.lexer.Expect(js_lexer.TCloseParen)
 
 	p.allowIn = oldAllowIn
 	return js_ast.Expr{Loc: loc, Data: &js_ast.EImportCall{
-		Expr:                    value,
-		OptionsOrNil:            optionsOrNil,
-		LeadingInteriorComments: comments,
+		Expr:            value,
+		OptionsOrNil:    optionsOrNil,
+		WebpackComments: webpackComments,
 	}}
 }
 
@@ -7256,7 +7257,7 @@ func (p *parser) parseStmtsUpTo(end js_lexer.T, opts parseStmtOpts) []js_ast.Stm
 
 	for {
 		// Preserve some statement-level comments
-		comments := p.lexer.CommentsToPreserveBefore
+		comments := p.lexer.LegalCommentsBeforeToken
 		if len(comments) > 0 {
 			for _, comment := range comments {
 				stmts = append(stmts, js_ast.Stmt{
@@ -14054,8 +14055,8 @@ func (p *parser) visitExprInOut(expr js_ast.Expr, in exprIn) (js_ast.Expr, exprO
 				}
 				p.importRecordsForCurrentPart = append(p.importRecordsForCurrentPart, importRecordIndex)
 				return js_ast.Expr{Loc: expr.Loc, Data: &js_ast.EImportString{
-					ImportRecordIndex:       importRecordIndex,
-					LeadingInteriorComments: e.LeadingInteriorComments,
+					ImportRecordIndex: importRecordIndex,
+					WebpackComments:   e.WebpackComments,
 				}}
 			}
 
@@ -14108,9 +14109,9 @@ func (p *parser) visitExprInOut(expr js_ast.Expr, in exprIn) (js_ast.Expr, exprO
 			}
 
 			return js_ast.Expr{Loc: expr.Loc, Data: &js_ast.EImportCall{
-				Expr:                    arg,
-				OptionsOrNil:            e.OptionsOrNil,
-				LeadingInteriorComments: e.LeadingInteriorComments,
+				Expr:            arg,
+				OptionsOrNil:    e.OptionsOrNil,
+				WebpackComments: e.WebpackComments,
 			}}
 		}), exprOut{}
 
diff --git a/internal/js_printer/js_printer.go b/internal/js_printer/js_printer.go
index 5acbad873f7..9119f80a808 100644
--- a/internal/js_printer/js_printer.go
+++ b/internal/js_printer/js_printer.go
@@ -1090,7 +1090,7 @@ func (p *printer) printQuotedUTF16(data []uint16, allowBacktick bool) {
 
 func (p *printer) printRequireOrImportExpr(
 	importRecordIndex uint32,
-	leadingInteriorComments []js_ast.Comment,
+	webpackComments []js_ast.Comment,
 	level js_ast.L,
 	flags printExprFlags,
 ) {
@@ -1175,10 +1175,10 @@ func (p *printer) printRequireOrImportExpr(
 			p.print("(")
 			defer p.print(")")
 		}
-		if len(leadingInteriorComments) > 0 {
+		if len(webpackComments) > 0 {
 			p.printNewline()
 			p.options.Indent++
-			for _, comment := range leadingInteriorComments {
+			for _, comment := range webpackComments {
 				p.printIndentedComment(comment.Text)
 			}
 			p.printIndent()
@@ -1188,7 +1188,7 @@ func (p *printer) printRequireOrImportExpr(
 		if !p.options.UnsupportedFeatures.Has(compat.DynamicImport) {
 			p.printImportCallAssertions(record.Assertions)
 		}
-		if len(leadingInteriorComments) > 0 {
+		if len(webpackComments) > 0 {
 			p.printNewline()
 			p.options.Indent--
 			p.printIndent()
@@ -1915,17 +1915,17 @@ func (p *printer) printExpr(expr js_ast.Expr, level js_ast.L, flags printExprFla
 		}
 
 	case *js_ast.EImportString:
-		var leadingInteriorComments []js_ast.Comment
+		var webpackComments []js_ast.Comment
 		if !p.options.MinifyWhitespace {
-			leadingInteriorComments = e.LeadingInteriorComments
+			webpackComments = e.WebpackComments
 		}
 		p.addSourceMapping(expr.Loc)
-		p.printRequireOrImportExpr(e.ImportRecordIndex, leadingInteriorComments, level, flags)
+		p.printRequireOrImportExpr(e.ImportRecordIndex, webpackComments, level, flags)
 
 	case *js_ast.EImportCall:
-		var leadingInteriorComments []js_ast.Comment
+		var webpackComments []js_ast.Comment
 		if !p.options.MinifyWhitespace {
-			leadingInteriorComments = e.LeadingInteriorComments
+			webpackComments = e.WebpackComments
 		}
 		wrap := level >= js_ast.LNew || (flags&forbidCall) != 0
 		if wrap {
@@ -1934,10 +1934,10 @@ func (p *printer) printExpr(expr js_ast.Expr, level js_ast.L, flags printExprFla
 		p.printSpaceBeforeIdentifier()
 		p.addSourceMapping(expr.Loc)
 		p.print("import(")
-		if len(leadingInteriorComments) > 0 {
+		if len(webpackComments) > 0 {
 			p.printNewline()
 			p.options.Indent++
-			for _, comment := range leadingInteriorComments {
+			for _, comment := range webpackComments {
 				p.printIndentedComment(comment.Text)
 			}
 			p.printIndent()
@@ -1947,7 +1947,7 @@ func (p *printer) printExpr(expr js_ast.Expr, level js_ast.L, flags printExprFla
 		// Just omit import assertions if they aren't supported
 		if e.OptionsOrNil.Data != nil && !p.options.UnsupportedFeatures.Has(compat.ImportAssertions) {
 			p.print(",")
-			if len(leadingInteriorComments) > 0 {
+			if len(webpackComments) > 0 {
 				p.printNewline()
 				p.printIndent()
 			} else {
@@ -1956,7 +1956,7 @@ func (p *printer) printExpr(expr js_ast.Expr, level js_ast.L, flags printExprFla
 			p.printExpr(e.OptionsOrNil, js_ast.LComma, 0)
 		}
 
-		if len(leadingInteriorComments) > 0 {
+		if len(webpackComments) > 0 {
 			p.printNewline()
 			p.options.Indent--
 			p.printIndent()
diff --git a/internal/js_printer/js_printer_test.go b/internal/js_printer/js_printer_test.go
index c25f148b554..093102320a0 100644
--- a/internal/js_printer/js_printer_test.go
+++ b/internal/js_printer/js_printer_test.go
@@ -667,13 +667,23 @@ func TestPrivateIdentifiers(t *testing.T) {
 func TestImport(t *testing.T) {
 	expectPrinted(t, "import('path');", "import(\"path\");\n") // The semicolon must not be a separate statement
 
-	// Test preservation of leading interior comments
-	expectPrinted(t, "import(// comment 1\n // comment 2\n 'path');", "import(\n  // comment 1\n  // comment 2\n  \"path\"\n);\n")
-	expectPrinted(t, "import(// comment 1\n // comment 2\n 'path', {type: 'module'});", "import(\n  // comment 1\n  // comment 2\n  \"path\",\n  { type: \"module\" }\n);\n")
-	expectPrinted(t, "import(/* comment 1 */ /* comment 2 */ 'path');", "import(\n  /* comment 1 */\n  /* comment 2 */\n  \"path\"\n);\n")
-	expectPrinted(t, "import(/* comment 1 */ /* comment 2 */ 'path', {type: 'module'});", "import(\n  /* comment 1 */\n  /* comment 2 */\n  \"path\",\n  { type: \"module\" }\n);\n")
-	expectPrinted(t, "import(\n    /* multi\n     * line\n     * comment */ 'path');", "import(\n  /* multi\n   * line\n   * comment */\n  \"path\"\n);\n")
-	expectPrinted(t, "import(/* comment 1 */ 'path' /* comment 2 */);", "import(\n  /* comment 1 */\n  \"path\"\n);\n")
+	// Test preservation of Webpack-specific comments
+	expectPrinted(t, "import(// webpackFoo: 1\n // webpackBar: 2\n 'path');", "import(\n  // webpackFoo: 1\n  // webpackBar: 2\n  \"path\"\n);\n")
+	expectPrinted(t, "import(// webpackFoo: 1\n // webpackBar: 2\n 'path', {type: 'module'});", "import(\n  // webpackFoo: 1\n  // webpackBar: 2\n  \"path\",\n  { type: \"module\" }\n);\n")
+	expectPrinted(t, "import(/* webpackFoo: 1 */ /* webpackBar: 2 */ 'path');", "import(\n  /* webpackFoo: 1 */\n  /* webpackBar: 2 */\n  \"path\"\n);\n")
+	expectPrinted(t, "import(/* webpackFoo: 1 */ /* webpackBar: 2 */ 'path', {type: 'module'});", "import(\n  /* webpackFoo: 1 */\n  /* webpackBar: 2 */\n  \"path\",\n  { type: \"module\" }\n);\n")
+	expectPrinted(t, "import(\n    /* multi\n     * line\n     * webpackBar: */ 'path');", "import(\n  /* multi\n   * line\n   * webpackBar: */\n  \"path\"\n);\n")
+	expectPrinted(t, "import(/* webpackFoo: 1 */ 'path' /* webpackBar:2 */);", "import(\n  /* webpackFoo: 1 */\n  /* webpackBar:2 */\n  \"path\"\n);\n")
+	expectPrinted(t, "import(/* webpackFoo: 1 */ 'path' /* webpackBar:2 */ ,);", "import(\n  /* webpackFoo: 1 */\n  /* webpackBar:2 */\n  \"path\"\n);\n")
+	expectPrinted(t, "import(/* webpackFoo: 1 */ 'path', /* webpackBar:2 */ );", "import(\n  /* webpackFoo: 1 */\n  /* webpackBar:2 */\n  \"path\"\n);\n")
+	expectPrinted(t, "import(/* webpackFoo: 1 */ 'path', { type: 'module' } /* webpackBar:2 */ );", "import(\n  /* webpackFoo: 1 */\n  /* webpackBar:2 */\n  \"path\",\n  { type: \"module\" }\n);\n")
+	expectPrinted(t, "import(new URL('path', /* webpackFoo: these can go anywhere */ import.meta.url))", "import(\n  /* webpackFoo: these can go anywhere */\n  new URL(\"path\", import.meta.url)\n);\n")
+
+	// Other comments should not be preserved
+	expectPrinted(t, "import(// comment 1\n // comment 2\n 'path');", "import(\"path\");\n")
+	expectPrinted(t, "import(// comment 1\n // comment 2\n 'path', {type: 'module'});", "import(\"path\", { type: \"module\" });\n")
+	expectPrinted(t, "import(/* comment 1 */ /* comment 2 */ 'path');", "import(\"path\");\n")
+	expectPrinted(t, "import(/* comment 1 */ /* comment 2 */ 'path', {type: 'module'});", "import(\"path\", { type: \"module\" });\n")
 }
 
 func TestExportDefault(t *testing.T) {