diff --git a/buildSrc/src/main/java/org/springframework/boot/build/bom/BomExtension.java b/buildSrc/src/main/java/org/springframework/boot/build/bom/BomExtension.java
index 5b450e79f90..2eefe89e1a1 100644
--- a/buildSrc/src/main/java/org/springframework/boot/build/bom/BomExtension.java
+++ b/buildSrc/src/main/java/org/springframework/boot/build/bom/BomExtension.java
@@ -21,6 +21,7 @@ import java.io.IOException;
 import java.io.InputStreamReader;
 import java.nio.charset.StandardCharsets;
 import java.util.ArrayList;
+import java.util.Collection;
 import java.util.HashMap;
 import java.util.LinkedHashMap;
 import java.util.List;
@@ -248,8 +249,8 @@ public class BomExtension {
 		public void prohibit(Action<ProhibitedHandler> action) {
 			ProhibitedHandler handler = new ProhibitedHandler();
 			action.execute(handler);
-			this.prohibitedVersions.add(
-					new ProhibitedVersion(handler.versionRange, handler.endsWith, handler.contains, handler.reason));
+			this.prohibitedVersions.add(new ProhibitedVersion(handler.versionRange, handler.startsWith,
+					handler.endsWith, handler.contains, handler.reason));
 		}
 
 		public void dependencyVersions(Action<DependencyVersionsHandler> action) {
@@ -273,9 +274,11 @@ public class BomExtension {
 
 			private String reason;
 
-			private String endsWith;
+			private final List<String> startsWith = new ArrayList<>();
 
-			private String contains;
+			private final List<String> endsWith = new ArrayList<>();
+
+			private final List<String> contains = new ArrayList<>();
 
 			private VersionRange versionRange;
 
@@ -288,12 +291,28 @@ public class BomExtension {
 				}
 			}
 
+			public void startsWith(String startsWith) {
+				this.startsWith.add(startsWith);
+			}
+
+			public void startsWith(Collection<String> startsWith) {
+				this.startsWith.addAll(startsWith);
+			}
+
 			public void endsWith(String endsWith) {
-				this.endsWith = endsWith;
+				this.endsWith.add(endsWith);
+			}
+
+			public void endsWith(Collection<String> endsWith) {
+				this.endsWith.addAll(endsWith);
 			}
 
 			public void contains(String contains) {
-				this.contains = contains;
+				this.contains.add(contains);
+			}
+
+			public void contains(List<String> contains) {
+				this.contains.addAll(contains);
 			}
 
 			public void because(String because) {
diff --git a/buildSrc/src/main/java/org/springframework/boot/build/bom/Library.java b/buildSrc/src/main/java/org/springframework/boot/build/bom/Library.java
index aa9ca236a68..a7a9d8a83ab 100644
--- a/buildSrc/src/main/java/org/springframework/boot/build/bom/Library.java
+++ b/buildSrc/src/main/java/org/springframework/boot/build/bom/Library.java
@@ -104,14 +104,18 @@ public class Library {
 
 		private final VersionRange range;
 
-		private final String endsWith;
+		private final List<String> startsWith;
 
-		private final String contains;
+		private final List<String> endsWith;
+
+		private final List<String> contains;
 
 		private final String reason;
 
-		public ProhibitedVersion(VersionRange range, String endsWith, String contains, String reason) {
+		public ProhibitedVersion(VersionRange range, List<String> startsWith, List<String> endsWith,
+				List<String> contains, String reason) {
 			this.range = range;
+			this.startsWith = startsWith;
 			this.endsWith = endsWith;
 			this.contains = contains;
 			this.reason = reason;
@@ -121,11 +125,15 @@ public class Library {
 			return this.range;
 		}
 
-		public String getEndsWith() {
+		public List<String> getStartsWith() {
+			return this.startsWith;
+		}
+
+		public List<String> getEndsWith() {
 			return this.endsWith;
 		}
 
-		public String getContains() {
+		public List<String> getContains() {
 			return this.contains;
 		}
 
diff --git a/buildSrc/src/main/java/org/springframework/boot/build/bom/bomr/InteractiveUpgradeResolver.java b/buildSrc/src/main/java/org/springframework/boot/build/bom/bomr/InteractiveUpgradeResolver.java
index a02d06933a7..27f3aa9c6f0 100644
--- a/buildSrc/src/main/java/org/springframework/boot/build/bom/bomr/InteractiveUpgradeResolver.java
+++ b/buildSrc/src/main/java/org/springframework/boot/build/bom/bomr/InteractiveUpgradeResolver.java
@@ -167,21 +167,26 @@ public final class InteractiveUpgradeResolver implements UpgradeResolver {
 	}
 
 	private boolean isPermitted(DependencyVersion dependencyVersion, List<ProhibitedVersion> prohibitedVersions) {
-		if (prohibitedVersions.isEmpty()) {
-			return true;
-		}
 		for (ProhibitedVersion prohibitedVersion : prohibitedVersions) {
+			String dependencyVersionToString = dependencyVersion.toString();
 			if (prohibitedVersion.getRange() != null && prohibitedVersion.getRange()
-					.containsVersion(new DefaultArtifactVersion(dependencyVersion.toString()))) {
+					.containsVersion(new DefaultArtifactVersion(dependencyVersionToString))) {
 				return false;
 			}
-			if (prohibitedVersion.getEndsWith() != null
-					&& dependencyVersion.toString().endsWith(prohibitedVersion.getEndsWith())) {
-				return false;
+			for (String startsWith : prohibitedVersion.getStartsWith()) {
+				if (dependencyVersionToString.startsWith(startsWith)) {
+					return false;
+				}
 			}
-			if (prohibitedVersion.getContains() != null
-					&& dependencyVersion.toString().contains(prohibitedVersion.getContains())) {
-				return false;
+			for (String endsWith : prohibitedVersion.getEndsWith()) {
+				if (dependencyVersionToString.endsWith(endsWith)) {
+					return false;
+				}
+			}
+			for (String contains : prohibitedVersion.getContains()) {
+				if (dependencyVersionToString.contains(contains)) {
+					return false;
+				}
 			}
 		}
 		return true;
diff --git a/spring-boot-project/spring-boot-dependencies/build.gradle b/spring-boot-project/spring-boot-dependencies/build.gradle
index f5a70334412..0c18279d846 100644
--- a/spring-boot-project/spring-boot-dependencies/build.gradle
+++ b/spring-boot-project/spring-boot-dependencies/build.gradle
@@ -1362,13 +1362,7 @@ bom {
 			endsWith ".jre8-preview"
 		}
 		prohibit {
-			contains ".jre11"
-		}
-		prohibit {
-			contains ".jre16"
-		}
-		prohibit {
-			contains ".jre17"
+			contains([".jre11", ".jre16", ".jre17"])
 		}
 		group("com.microsoft.sqlserver") {
 			modules = [