diff --git a/processor/src/main/java/org/mapstruct/ap/internal/model/source/selector/SelectionCriteria.java b/processor/src/main/java/org/mapstruct/ap/internal/model/source/selector/SelectionCriteria.java
index b70e94b6d..da8bae365 100644
--- a/processor/src/main/java/org/mapstruct/ap/internal/model/source/selector/SelectionCriteria.java
+++ b/processor/src/main/java/org/mapstruct/ap/internal/model/source/selector/SelectionCriteria.java
@@ -6,6 +6,7 @@
 package org.mapstruct.ap.internal.model.source.selector;
 
 import java.util.ArrayList;
+import java.util.Collections;
 import java.util.List;
 
 import javax.lang.model.type.TypeMirror;
@@ -26,6 +27,7 @@ public class SelectionCriteria {
     private final String targetPropertyName;
     private final TypeMirror qualifyingResultType;
     private final SourceRHS sourceRHS;
+    private boolean ignoreQualifiers = false;
     private Type type;
     private final boolean allowDirect;
     private final boolean allowConversion;
@@ -87,12 +89,16 @@ public class SelectionCriteria {
         return type == Type.PRESENCE_CHECK;
     }
 
+    public void setIgnoreQualifiers(boolean ignoreQualifiers) {
+        this.ignoreQualifiers = ignoreQualifiers;
+    }
+
     public List<TypeMirror> getQualifiers() {
-        return qualifiers;
+        return ignoreQualifiers ? Collections.emptyList() : qualifiers;
     }
 
     public List<String> getQualifiedByNames() {
-        return qualifiedByNames;
+        return ignoreQualifiers ? Collections.emptyList() : qualifiedByNames;
     }
 
     public String getTargetPropertyName() {
diff --git a/processor/src/main/java/org/mapstruct/ap/internal/processor/creation/MappingResolverImpl.java b/processor/src/main/java/org/mapstruct/ap/internal/processor/creation/MappingResolverImpl.java
index b971341fc..2e2a760bf 100755
--- a/processor/src/main/java/org/mapstruct/ap/internal/processor/creation/MappingResolverImpl.java
+++ b/processor/src/main/java/org/mapstruct/ap/internal/processor/creation/MappingResolverImpl.java
@@ -712,6 +712,11 @@ public class MappingResolverImpl implements MappingResolver {
         }
     }
 
+    private enum BestMatchType {
+        IGNORE_QUALIFIERS_BEFORE_Y_CANDIDATES,
+        IGNORE_QUALIFIERS_AFTER_Y_CANDIDATES,
+    }
+
     /**
      * Suppose mapping required from A to C and:
      * <ul>
@@ -743,6 +748,17 @@ public class MappingResolverImpl implements MappingResolver {
             if ( mmAttempt.hasResult ) {
                 return mmAttempt.result;
             }
+            if ( att.hasQualfiers() ) {
+                mmAttempt = mmAttempt.getBestMatchIgnoringQualifiersBeforeY( sourceType, targetType );
+                if ( mmAttempt.hasResult ) {
+                    return mmAttempt.result;
+                }
+
+                mmAttempt = mmAttempt.getBestMatchIgnoringQualifiersAfterY( sourceType, targetType );
+                if ( mmAttempt.hasResult ) {
+                    return mmAttempt.result;
+                }
+            }
             MethodMethod<Method, BuiltInMethod> mbAttempt =
                 new MethodMethod<>( att, att.methods, att.builtIns, att::toMethodRef, att::toBuildInRef )
                     .getBestMatch( sourceType, targetType );
@@ -772,6 +788,18 @@ public class MappingResolverImpl implements MappingResolver {
         }
 
         private MethodMethod<T1, T2> getBestMatch(Type sourceType, Type targetType) {
+            return getBestMatch( sourceType, targetType, null );
+        }
+
+        private MethodMethod<T1, T2> getBestMatchIgnoringQualifiersBeforeY(Type sourceType, Type targetType) {
+            return getBestMatch( sourceType, targetType, BestMatchType.IGNORE_QUALIFIERS_BEFORE_Y_CANDIDATES );
+        }
+
+        private MethodMethod<T1, T2> getBestMatchIgnoringQualifiersAfterY(Type sourceType, Type targetType) {
+            return getBestMatch( sourceType, targetType, BestMatchType.IGNORE_QUALIFIERS_AFTER_Y_CANDIDATES );
+        }
+
+        private MethodMethod<T1, T2> getBestMatch(Type sourceType, Type targetType, BestMatchType matchType) {
 
             Set<T2> yCandidates = new HashSet<>();
             Map<SelectedMethod<T1>, List<SelectedMethod<T2>>> xCandidates = new LinkedHashMap<>();
@@ -784,6 +812,9 @@ public class MappingResolverImpl implements MappingResolver {
             // sourceMethod or builtIn that fits the signature B to C. Only then there is a match. If we have a match
             // a nested method call can be called. so C = methodY( methodX (A) )
             attempt.selectionCriteria.setPreferUpdateMapping( false );
+            attempt.selectionCriteria.setIgnoreQualifiers(
+                matchType == BestMatchType.IGNORE_QUALIFIERS_BEFORE_Y_CANDIDATES );
+
             for ( T2 yCandidate : yMethods ) {
                 Type ySourceType = yCandidate.getMappingSourceType();
                 ySourceType = ySourceType.resolveParameterToType( targetType, yCandidate.getResultType() ).getMatch();
@@ -796,13 +827,16 @@ public class MappingResolverImpl implements MappingResolver {
                 }
                 List<SelectedMethod<T1>> xMatches = attempt.getBestMatch( xMethods, sourceType, ySourceType );
                 if ( !xMatches.isEmpty() ) {
-                    xMatches.stream().forEach( x -> xCandidates.put( x, new ArrayList<>() ) );
-                    final Type typeInTheMiddle = ySourceType;
-                    xMatches.stream().forEach( x -> typesInTheMiddle.put( x, typeInTheMiddle ) );
+                    for ( SelectedMethod<T1> x : xMatches ) {
+                        xCandidates.put( x, new ArrayList<>() );
+                        typesInTheMiddle.put( x, ySourceType );
+                    }
                     yCandidates.add( yCandidate );
                 }
             }
             attempt.selectionCriteria.setPreferUpdateMapping( true );
+            attempt.selectionCriteria.setIgnoreQualifiers(
+                matchType == BestMatchType.IGNORE_QUALIFIERS_AFTER_Y_CANDIDATES );
 
             // collect all results
             List<T2> yCandidatesList = new ArrayList<>( yCandidates );
@@ -816,6 +850,7 @@ public class MappingResolverImpl implements MappingResolver {
                 }
             }
 
+            attempt.selectionCriteria.setIgnoreQualifiers( false );
             // no results left
             if ( xCandidates.isEmpty() ) {
                 return this;
diff --git a/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/Group.java b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/Group.java
new file mode 100644
index 000000000..4451431fe
--- /dev/null
+++ b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/Group.java
@@ -0,0 +1,22 @@
+/*
+ * Copyright MapStruct Authors.
+ *
+ * Licensed under the Apache License version 2.0, available at http://www.apache.org/licenses/LICENSE-2.0
+ */
+package org.mapstruct.ap.test.bugs._2538;
+
+/**
+ * @author Filip Hrisafov
+ */
+public class Group {
+
+    private final String id;
+
+    public Group(String id) {
+        this.id = id;
+    }
+
+    public String getId() {
+        return id;
+    }
+}
diff --git a/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/GroupDto.java b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/GroupDto.java
new file mode 100644
index 000000000..0d94c9081
--- /dev/null
+++ b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/GroupDto.java
@@ -0,0 +1,22 @@
+/*
+ * Copyright MapStruct Authors.
+ *
+ * Licensed under the Apache License version 2.0, available at http://www.apache.org/licenses/LICENSE-2.0
+ */
+package org.mapstruct.ap.test.bugs._2538;
+
+/**
+ * @author Filip Hrisafov
+ */
+public class GroupDto {
+
+    private final String id;
+
+    public GroupDto(String id) {
+        this.id = id;
+    }
+
+    public String getId() {
+        return id;
+    }
+}
diff --git a/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/Issue2538Test.java b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/Issue2538Test.java
new file mode 100644
index 000000000..cf99e67f9
--- /dev/null
+++ b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/Issue2538Test.java
@@ -0,0 +1,39 @@
+/*
+ * Copyright MapStruct Authors.
+ *
+ * Licensed under the Apache License version 2.0, available at http://www.apache.org/licenses/LICENSE-2.0
+ */
+package org.mapstruct.ap.test.bugs._2538;
+
+import org.mapstruct.ap.testutil.ProcessorTest;
+import org.mapstruct.ap.testutil.WithClasses;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * @author Filip Hrisafov
+ */
+@WithClasses({
+    Group.class,
+    GroupDto.class,
+    TeamMapper.class,
+    TeamRole.class,
+    TeamRoleDto.class,
+})
+class Issue2538Test {
+
+    @ProcessorTest
+    void shouldCorrectlyUseQualifiedMethodIn2StepMapping() {
+        TeamRole role = TeamMapper.INSTANCE.mapUsingFirstLookup( new TeamRoleDto( "test" ) );
+
+        assertThat( role ).isNotNull();
+        assertThat( role.getGroup() ).isNotNull();
+        assertThat( role.getGroup().getId() ).isEqualTo( "lookup-test" );
+
+        role = TeamMapper.INSTANCE.mapUsingSecondLookup( new TeamRoleDto( "test" ) );
+
+        assertThat( role ).isNotNull();
+        assertThat( role.getGroup() ).isNotNull();
+        assertThat( role.getGroup().getId() ).isEqualTo( "second-test" );
+    }
+}
diff --git a/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamMapper.java b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamMapper.java
new file mode 100644
index 000000000..5615e7bc4
--- /dev/null
+++ b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamMapper.java
@@ -0,0 +1,42 @@
+/*
+ * Copyright MapStruct Authors.
+ *
+ * Licensed under the Apache License version 2.0, available at http://www.apache.org/licenses/LICENSE-2.0
+ */
+package org.mapstruct.ap.test.bugs._2538;
+
+import org.mapstruct.Mapper;
+import org.mapstruct.Mapping;
+import org.mapstruct.Named;
+import org.mapstruct.factory.Mappers;
+
+@Mapper
+public interface TeamMapper {
+
+    TeamMapper INSTANCE = Mappers.getMapper( TeamMapper.class );
+
+    // This method is testing methodX(methodY(...)) where methodY is qualified
+    @Mapping(target = "group", source = "groupId", qualifiedByName = "firstLookup")
+    TeamRole mapUsingFirstLookup(TeamRoleDto in);
+
+    // This method is testing methodX(methodY(...)) where methodX is qualified
+    @Mapping(target = "group", source = "groupId", qualifiedByName = "secondLookup")
+    TeamRole mapUsingSecondLookup(TeamRoleDto in);
+
+    Group map(GroupDto in);
+
+    @Named("firstLookup")
+    default GroupDto lookupGroup(String groupId) {
+        return groupId != null ? new GroupDto( "lookup-" + groupId ) : null;
+    }
+
+    default GroupDto normalLookup(String groupId) {
+        return groupId != null ? new GroupDto( groupId ) : null;
+    }
+
+    @Named("secondLookup")
+    default Group mapSecondLookup(GroupDto in) {
+        return in != null ? new Group( "second-" + in.getId() ) : null;
+    }
+
+}
diff --git a/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamRole.java b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamRole.java
new file mode 100644
index 000000000..f73700fa4
--- /dev/null
+++ b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamRole.java
@@ -0,0 +1,22 @@
+/*
+ * Copyright MapStruct Authors.
+ *
+ * Licensed under the Apache License version 2.0, available at http://www.apache.org/licenses/LICENSE-2.0
+ */
+package org.mapstruct.ap.test.bugs._2538;
+
+/**
+ * @author Filip Hrisafov
+ */
+public class TeamRole {
+
+    private final Group group;
+
+    public TeamRole(Group group) {
+        this.group = group;
+    }
+
+    public Group getGroup() {
+        return group;
+    }
+}
diff --git a/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamRoleDto.java b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamRoleDto.java
new file mode 100644
index 000000000..fac5a1a9e
--- /dev/null
+++ b/processor/src/test/java/org/mapstruct/ap/test/bugs/_2538/TeamRoleDto.java
@@ -0,0 +1,22 @@
+/*
+ * Copyright MapStruct Authors.
+ *
+ * Licensed under the Apache License version 2.0, available at http://www.apache.org/licenses/LICENSE-2.0
+ */
+package org.mapstruct.ap.test.bugs._2538;
+
+/**
+ * @author Filip Hrisafov
+ */
+public class TeamRoleDto {
+
+    private final String groupId;
+
+    public TeamRoleDto(String groupId) {
+        this.groupId = groupId;
+    }
+
+    public String getGroupId() {
+        return groupId;
+    }
+}