diff --git a/bundles/org.eclipse.ui.workbench.texteditor/src/org/eclipse/ui/internal/findandreplace/FindReplaceLogic.java b/bundles/org.eclipse.ui.workbench.texteditor/src/org/eclipse/ui/internal/findandreplace/FindReplaceLogic.java
index 8cf7db6e0e9..fadff8e1f21 100644
--- a/bundles/org.eclipse.ui.workbench.texteditor/src/org/eclipse/ui/internal/findandreplace/FindReplaceLogic.java
+++ b/bundles/org.eclipse.ui.workbench.texteditor/src/org/eclipse/ui/internal/findandreplace/FindReplaceLogic.java
@@ -18,6 +18,7 @@
 import java.util.HashSet;
 import java.util.List;
 import java.util.Set;
+import java.util.regex.Pattern;
 import java.util.regex.PatternSyntaxException;
 
 import org.eclipse.swt.custom.BusyIndicator;
@@ -582,13 +583,26 @@ public boolean performReplaceAndFind(String findString, String replaceString) {
 	@Override
 	public boolean performSelectAndReplace(String findString, String replaceString) {
 		resetStatus();
-		boolean needToSelectFirst = !getCurrentSelection().equals(findString);
-		if (needToSelectFirst) {
+		if (!isFindStringSelected(findString)) {
 			performSearch(findString);
 		}
 		return replaceSelection(replaceString);
 	}
 
+	private boolean isFindStringSelected(String findString) {
+		String selectedString = getCurrentSelection();
+		if (isRegExSearchAvailableAndActive()) {
+			int patternFlags = 0;
+			if (!isActive(SearchOptions.CASE_SENSITIVE)) {
+				patternFlags |= Pattern.CASE_INSENSITIVE | Pattern.UNICODE_CASE;
+			}
+			Pattern pattern = Pattern.compile(findString, patternFlags);
+			return pattern.matcher(selectedString).find();
+		} else {
+			return getCurrentSelection().equals(findString);
+		}
+	}
+
 	@Override
 	public void updateTarget(IFindReplaceTarget newTarget, boolean canEditTarget) {
 		resetStatus();
diff --git a/tests/org.eclipse.ui.workbench.texteditor.tests/src/org/eclipse/ui/internal/findandreplace/FindReplaceLogicTest.java b/tests/org.eclipse.ui.workbench.texteditor.tests/src/org/eclipse/ui/internal/findandreplace/FindReplaceLogicTest.java
index 8a8cf22bf31..b5aa6720efc 100644
--- a/tests/org.eclipse.ui.workbench.texteditor.tests/src/org/eclipse/ui/internal/findandreplace/FindReplaceLogicTest.java
+++ b/tests/org.eclipse.ui.workbench.texteditor.tests/src/org/eclipse/ui/internal/findandreplace/FindReplaceLogicTest.java
@@ -19,6 +19,7 @@
 import static org.hamcrest.Matchers.instanceOf;
 import static org.hamcrest.Matchers.is;
 import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertTrue;
 
 import org.junit.After;
 import org.junit.Before;
@@ -196,6 +197,98 @@ public void testPerformSelectAndReplace() {
 		expectStatusEmpty(findReplaceLogic);
 	}
 
+	@Test
+	public void testPerformSelectAndReplaceRegEx() {
+		TextViewer textViewer= setupTextViewer("Hello<replace>World<replace>!");
+		IFindReplaceLogic findReplaceLogic= setupFindReplaceLogicObject(textViewer);
+		findReplaceLogic.activate(SearchOptions.FORWARD);
+		findReplaceLogic.activate(SearchOptions.REGEX);
+
+		findReplaceLogic.performSearch("<(\\w*)>");
+		boolean status= findReplaceLogic.performSelectAndReplace("<(\\w*)>", " ");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("Hello World<replace>!"));
+		expectStatusEmpty(findReplaceLogic);
+
+		status= findReplaceLogic.performSelectAndReplace("<(\\w*)>", " ");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("Hello World !"));
+		expectStatusEmpty(findReplaceLogic);
+
+		status= findReplaceLogic.performSelectAndReplace("<(\\w*)>", " ");
+		assertEquals("Status wasn't correctly returned", false, status);
+		assertEquals("Text shouldn't have been changed", "Hello World !", textViewer.getDocument().get());
+		expectStatusIsCode(findReplaceLogic, FindStatus.StatusCode.NO_MATCH);
+	}
+
+	@Test
+	public void testPerformSelectAndReplaceRegExWithLinebreaks() {
+		TextViewer textViewer= setupTextViewer("""
+				Hello
+				World
+				!""");
+		IFindReplaceLogic findReplaceLogic= setupFindReplaceLogicObject(textViewer);
+		findReplaceLogic.activate(SearchOptions.FORWARD);
+		findReplaceLogic.activate(SearchOptions.REGEX);
+		findReplaceLogic.deactivate(SearchOptions.WRAP);
+
+		assertTrue(findReplaceLogic.performSearch("o$"));
+		boolean status= findReplaceLogic.performSelectAndReplace("o$", "o!");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("""
+				Hello!
+				World
+				!"""));
+		expectStatusEmpty(findReplaceLogic);
+
+		status= findReplaceLogic.performSelectAndReplace("""
+				d
+				!""", "d!");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("""
+				Hello!
+				World!"""));
+		expectStatusEmpty(findReplaceLogic);
+
+		status= findReplaceLogic.performSelectAndReplace("""
+				""", " ");
+		assertEquals("Status wasn't correctly returned", false, status);
+		assertEquals("Text shouldn't have been changed", """
+				Hello!
+				World!""", textViewer.getDocument().get());
+	}
+
+	@Test
+	public void testPerformSelectAndReplaceWithConfigurationChanges() {
+		TextViewer textViewer= setupTextViewer("Hello<replace>World<replace>!<replace>!");
+		IFindReplaceLogic findReplaceLogic= setupFindReplaceLogicObject(textViewer);
+		findReplaceLogic.activate(SearchOptions.FORWARD);
+		findReplaceLogic.activate(SearchOptions.REGEX);
+
+		findReplaceLogic.performSearch("<(\\w*)>");
+		boolean status= findReplaceLogic.performSelectAndReplace("<(\\w*)>", " ");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("Hello World<replace>!<replace>!"));
+		expectStatusEmpty(findReplaceLogic);
+
+		findReplaceLogic.deactivate(SearchOptions.REGEX);
+		status= findReplaceLogic.performSelectAndReplace("<replace>", " ");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("Hello World !<replace>!"));
+		expectStatusEmpty(findReplaceLogic);
+
+		findReplaceLogic.activate(SearchOptions.REGEX);
+		status= findReplaceLogic.performSelectAndReplace("<(\\w*)>", " ");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("Hello World ! !"));
+		expectStatusEmpty(findReplaceLogic);
+
+		status= findReplaceLogic.performSelectAndReplace("<(\\w*)>", " ");
+		assertEquals("Status wasn't correctly returned", false, status);
+		assertEquals("Text shouldn't have been changed", "Hello World ! !", textViewer.getDocument().get());
+		expectStatusIsCode(findReplaceLogic, FindStatus.StatusCode.NO_MATCH);
+	}
+
 	@Test
 	public void testPerformSelectAndReplaceBackward() {
 		TextViewer textViewer= setupTextViewer("Hello<replace>World<replace>!");
@@ -213,7 +306,6 @@ public void testPerformSelectAndReplaceBackward() {
 		expectStatusEmpty(findReplaceLogic);
 	}
 
-
 	@Test
 	public void testPerformReplaceAndFind() {
 		TextViewer textViewer= setupTextViewer("Hello<replace>World<replace>!");
@@ -237,6 +329,36 @@ public void testPerformReplaceAndFind() {
 		expectStatusIsCode(findReplaceLogic, FindStatus.StatusCode.NO_MATCH);
 	}
 
+	@Test
+	public void testPerformReplaceAndFindRegEx() {
+		TextViewer textViewer= setupTextViewer("Hello<replace>World<replace>!<r>!");
+		IFindReplaceLogic findReplaceLogic= setupFindReplaceLogicObject(textViewer);
+		findReplaceLogic.activate(SearchOptions.FORWARD);
+		findReplaceLogic.activate(SearchOptions.REGEX);
+
+		boolean status= findReplaceLogic.performReplaceAndFind("<(\\w*)>", " ");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("Hello World<replace>!<r>!"));
+		assertThat(findReplaceLogic.getTarget().getSelectionText(), equalTo("<replace>"));
+		expectStatusEmpty(findReplaceLogic);
+
+		status= findReplaceLogic.performReplaceAndFind("<(\\w*)>", " ");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("Hello World !<r>!"));
+		assertThat(findReplaceLogic.getTarget().getSelectionText(), equalTo("<r>"));
+		expectStatusEmpty(findReplaceLogic);
+
+		status= findReplaceLogic.performReplaceAndFind("<(\\w)>", " ");
+		assertTrue(status);
+		assertThat(textViewer.getDocument().get(), equalTo("Hello World ! !"));
+		expectStatusIsCode(findReplaceLogic, FindStatus.StatusCode.NO_MATCH);
+
+		status= findReplaceLogic.performReplaceAndFind("<(\\w*)>", " ");
+		assertEquals("Status wasn't correctly returned", false, status);
+		assertEquals("Text shouldn't have been changed", "Hello World ! !", textViewer.getDocument().get());
+		expectStatusIsCode(findReplaceLogic, FindStatus.StatusCode.NO_MATCH);
+	}
+
 	@Test
 	public void testPerformSelectAllForward() {
 		TextViewer textViewer= setupTextViewer("AbAbAbAb");