diff --git a/internal/css_ast/css_ast.go b/internal/css_ast/css_ast.go
index 3ff285fd7f9..50bd0a09998 100644
--- a/internal/css_ast/css_ast.go
+++ b/internal/css_ast/css_ast.go
@@ -432,8 +432,22 @@ func (r *RAtCharset) Hash() (uint32, bool) {
 	return hash, true
 }
 
+type ImportConditions struct {
+	Layers   []Token
+	Supports []Token
+	Media    []Token
+}
+
+func (conditions *ImportConditions) CloneWithImportRecords(importRecordsIn []ast.ImportRecord, importRecordsOut []ast.ImportRecord) (*ImportConditions, []ast.ImportRecord) {
+	result := ImportConditions{}
+	result.Layers, importRecordsOut = CloneTokensWithImportRecords(conditions.Layers, importRecordsIn, nil, importRecordsOut)
+	result.Supports, importRecordsOut = CloneTokensWithImportRecords(conditions.Supports, importRecordsIn, nil, importRecordsOut)
+	result.Media, importRecordsOut = CloneTokensWithImportRecords(conditions.Media, importRecordsIn, nil, importRecordsOut)
+	return &result, importRecordsOut
+}
+
 type RAtImport struct {
-	ImportConditions  []Token
+	ImportConditions  *ImportConditions
 	ImportRecordIndex uint32
 }
 
diff --git a/internal/css_parser/css_parser.go b/internal/css_parser/css_parser.go
index 40cdf14cb38..dcf6ef31689 100644
--- a/internal/css_parser/css_parser.go
+++ b/internal/css_parser/css_parser.go
@@ -1141,6 +1141,7 @@ abortRuleParser:
 			kind = atRuleEmpty
 			p.eat(css_lexer.TWhitespace)
 			if path, r, ok := p.expectURLOrString(); ok {
+				var conditions css_ast.ImportConditions
 				importConditionsStart := p.index
 				for {
 					if kind := p.current().Kind; kind == css_lexer.TSemicolon || kind == css_lexer.TOpenBrace ||
@@ -1152,16 +1153,39 @@ abortRuleParser:
 				if p.current().Kind == css_lexer.TOpenBrace {
 					break // Avoid parsing an invalid "@import" rule
 				}
-				importConditions := p.convertTokens(p.tokens[importConditionsStart:p.index])
+				conditions.Media = p.convertTokens(p.tokens[importConditionsStart:p.index])
 				kind := ast.ImportAt
 
 				// Insert or remove whitespace before the first token
-				if len(importConditions) > 0 {
+				var importConditions *css_ast.ImportConditions
+				if len(conditions.Media) > 0 {
 					kind = ast.ImportAtConditional
-					if p.options.minifyWhitespace {
-						importConditions[0].Whitespace &= ^css_ast.WhitespaceBefore
-					} else {
-						importConditions[0].Whitespace |= css_ast.WhitespaceBefore
+					importConditions = &conditions
+
+					// Handle "layer()"
+					if t := conditions.Media[0]; (t.Kind == css_lexer.TIdent || t.Kind == css_lexer.TFunction) && t.Text == "layer" {
+						conditions.Layers = conditions.Media[:1]
+						conditions.Media = conditions.Media[1:]
+					}
+
+					// Handle "supports()"
+					if len(conditions.Media) > 0 {
+						if t := conditions.Media[0]; t.Kind == css_lexer.TFunction && t.Text == "supports" {
+							conditions.Supports = conditions.Media[:1]
+							conditions.Media = conditions.Media[1:]
+						}
+					}
+
+					// Remove leading and trailing whitespace
+					if len(conditions.Layers) > 0 {
+						conditions.Layers[0].Whitespace &= ^(css_ast.WhitespaceBefore | css_ast.WhitespaceAfter)
+					}
+					if len(conditions.Supports) > 0 {
+						conditions.Supports[0].Whitespace &= ^(css_ast.WhitespaceBefore | css_ast.WhitespaceAfter)
+					}
+					if n := len(conditions.Media); n > 0 {
+						conditions.Media[0].Whitespace &= ^css_ast.WhitespaceBefore
+						conditions.Media[n-1].Whitespace &= ^css_ast.WhitespaceAfter
 					}
 				}
 
diff --git a/internal/css_printer/css_printer.go b/internal/css_printer/css_printer.go
index 6e396dd4fc1..08f805a3e17 100644
--- a/internal/css_printer/css_printer.go
+++ b/internal/css_printer/css_printer.go
@@ -170,7 +170,29 @@ func (p *printer) printRule(rule css_ast.Rule, indent int32, omitTrailingSemicol
 		}
 		p.printQuoted(record.Path.Text, flags)
 		p.recordImportPathForMetafile(r.ImportRecordIndex)
-		p.printTokens(r.ImportConditions, printTokensOpts{})
+		if conditions := r.ImportConditions; conditions != nil {
+			space := !p.options.MinifyWhitespace
+			if len(conditions.Layers) > 0 {
+				if space {
+					p.print(" ")
+				}
+				p.printTokens(conditions.Layers, printTokensOpts{})
+				space = true
+			}
+			if len(conditions.Supports) > 0 {
+				if space {
+					p.print(" ")
+				}
+				p.printTokens(conditions.Supports, printTokensOpts{})
+				space = true
+			}
+			if len(conditions.Media) > 0 {
+				if space {
+					p.print(" ")
+				}
+				p.printTokens(conditions.Media, printTokensOpts{})
+			}
+		}
 		p.print(";")
 
 	case *css_ast.RAtKeyframes:
diff --git a/internal/linker/linker.go b/internal/linker/linker.go
index 51f9e49c37a..e5f9ef8e71d 100644
--- a/internal/linker/linker.go
+++ b/internal/linker/linker.go
@@ -194,7 +194,7 @@ type chunkReprCSS struct {
 
 type externalImportCSS struct {
 	path                   logger.Path
-	conditions             []css_ast.Token
+	conditions             *css_ast.ImportConditions
 	conditionImportRecords []ast.ImportRecord
 }
 
@@ -3337,8 +3337,7 @@ func (c *linkerContext) findImportedCSSFilesInJSOrder(entryPoint uint32) (order
 // traversal order is B D C A.
 func (c *linkerContext) findImportedFilesInCSSOrder(entryPoints []uint32) (externalOrder []externalImportCSS, internalOrder []uint32) {
 	type externalImportsCSS struct {
-		conditions    [][]css_ast.Token
-		unconditional bool
+		conditions []css_ast.ImportConditions
 	}
 
 	visited := make(map[uint32]bool)
@@ -3376,32 +3375,40 @@ func (c *linkerContext) findImportedFilesInCSSOrder(entryPoints []uint32) (exter
 						// Record external dependencies
 						external := externals[record.Path]
 
-						// Check for an unconditional import. An unconditional import
-						// should always mask all conditional imports that are overridden
-						// by the unconditional import.
-						if external.unconditional {
-							continue
+						var before css_ast.ImportConditions
+						if conditions := atImport.ImportConditions; conditions != nil {
+							before = *conditions
 						}
 
-						if len(atImport.ImportConditions) == 0 {
-							external.unconditional = true
-						} else {
-							// Check for a conditional import. A conditional import does not
-							// mask an earlier unconditional import because re-evaluating a
-							// CSS file can have observable results.
-							for _, tokens := range external.conditions {
-								if css_ast.TokensEqualIgnoringWhitespace(tokens, atImport.ImportConditions) {
+						// Skip this rule if a later rule masks it
+						for _, after := range external.conditions {
+							if css_ast.TokensEqualIgnoringWhitespace(before.Layers, after.Layers) {
+								if len(after.Supports) == 0 && len(after.Media) == 0 {
+									// If the later one doesn't have any conditions, only keep
+									// the later one. The later one will mask the effects of the
+									// earlier one regardless of whether the earlier one has any
+									// conditions or not. Only do this if the layers are equal.
+									continue outer
+								}
+
+								// If the import conditions are exactly equal, then only keep
+								// the later one. The earlier one will have no effect.
+								if css_ast.TokensEqualIgnoringWhitespace(before.Supports, after.Supports) &&
+									css_ast.TokensEqualIgnoringWhitespace(before.Media, after.Media) {
 									continue outer
 								}
 							}
-							external.conditions = append(external.conditions, atImport.ImportConditions)
 						}
 
-						// Clone any import records associated with the condition tokens
-						conditions, conditionImportRecords := css_ast.CloneTokensWithImportRecords(
-							atImport.ImportConditions, repr.AST.ImportRecords, nil, nil)
-
+						external.conditions = append(external.conditions, before)
 						externals[record.Path] = external
+
+						var conditions *css_ast.ImportConditions
+						var conditionImportRecords []ast.ImportRecord
+						if atImport.ImportConditions != nil {
+							conditions, conditionImportRecords = atImport.ImportConditions.CloneWithImportRecords(repr.AST.ImportRecords, conditionImportRecords)
+						}
+
 						externalOrder = append(externalOrder, externalImportCSS{
 							path:                   record.Path,
 							conditions:             conditions,
@@ -5712,9 +5719,10 @@ func (c *linkerContext) generateChunkCSS(chunkIndex int, chunkWaitGroup *sync.Wa
 		// Insert all external "@import" rules at the front. In CSS, all "@import"
 		// rules must come first or the browser will just ignore them.
 		for _, external := range chunkRepr.externalImportsInOrder {
-			var conditions []css_ast.Token
-			conditions, tree.ImportRecords = css_ast.CloneTokensWithImportRecords(
-				external.conditions, external.conditionImportRecords, conditions, tree.ImportRecords)
+			var conditions *css_ast.ImportConditions
+			if external.conditions != nil {
+				conditions, tree.ImportRecords = external.conditions.CloneWithImportRecords(external.conditionImportRecords, tree.ImportRecords)
+			}
 			tree.Rules = append(tree.Rules, css_ast.Rule{Data: &css_ast.RAtImport{
 				ImportRecordIndex: uint32(len(tree.ImportRecords)),
 				ImportConditions:  conditions,