diff --git a/eclipse-language-servers/org.springframework.tooling.boot.java.ls/src/org/springframework/tooling/boot/java/ls/SpringBootJavaLanguageServer.java b/eclipse-language-servers/org.springframework.tooling.boot.java.ls/src/org/springframework/tooling/boot/java/ls/SpringBootJavaLanguageServer.java
index 64a87debd..5169ff4a5 100644
--- a/eclipse-language-servers/org.springframework.tooling.boot.java.ls/src/org/springframework/tooling/boot/java/ls/SpringBootJavaLanguageServer.java
+++ b/eclipse-language-servers/org.springframework.tooling.boot.java.ls/src/org/springframework/tooling/boot/java/ls/SpringBootJavaLanguageServer.java
@@ -39,7 +39,13 @@ public class SpringBootJavaLanguageServer extends STS4LanguageServerProcessStrea
 		commands.add("-Dlsp.completions.indentation.enable=true");
 		commands.add("-Xmx1024m");
 		commands.add("-cp");
-		commands.add(getToolsJAR() + File.pathSeparator + getLanguageServerJARLocation());
+		File toolsJar = getToolsJAR();
+		if (toolsJar!=null) {
+			commands.add(toolsJar + File.pathSeparator + getLanguageServerJARLocation());
+		} else {
+			//TODO: issue a 'missing tools.jar warning somehow depending on the platform?
+			commands.add(getLanguageServerJARLocation());
+		}
 		commands.add("org.springframework.boot.loader.JarLauncher");
 
 		String workingDir = getWorkingDirLocation();
diff --git a/eclipse-language-servers/org.springframework.tooling.ls.eclipse.commons/src/org/springframework/tooling/ls/eclipse/commons/STS4LanguageServerProcessStreamConnector.java b/eclipse-language-servers/org.springframework.tooling.ls.eclipse.commons/src/org/springframework/tooling/ls/eclipse/commons/STS4LanguageServerProcessStreamConnector.java
index e5e89c430..c362e0b21 100644
--- a/eclipse-language-servers/org.springframework.tooling.ls.eclipse.commons/src/org/springframework/tooling/ls/eclipse/commons/STS4LanguageServerProcessStreamConnector.java
+++ b/eclipse-language-servers/org.springframework.tooling.ls.eclipse.commons/src/org/springframework/tooling/ls/eclipse/commons/STS4LanguageServerProcessStreamConnector.java
@@ -12,8 +12,11 @@ package org.springframework.tooling.ls.eclipse.commons;
 
 import java.io.File;
 import java.io.IOException;
+import java.util.ArrayList;
+import java.util.List;
+import java.util.Optional;
+import java.util.function.Consumer;
 
-import org.eclipse.core.runtime.Path;
 import org.eclipse.jdt.internal.launching.StandardVMType;
 import org.eclipse.lsp4e.server.ProcessStreamConnectionProvider;
 
@@ -50,11 +53,58 @@ public class STS4LanguageServerProcessStreamConnector extends ProcessStreamConne
 		return null;
 	}
 	
-	protected String getToolsJAR() {
-		File jre = new File(System.getProperty("java.home"));
-		return new File(jre.getParent(), "lib" + Path.SEPARATOR + "tools.jar").getAbsolutePath();
+	/**
+	 * Different places to look for tools jar, relative to Java home.
+	 */
+	private static String [] TOOLS_JAR_PATHS = {
+			"../lib/tools.jar",
+			"lib/tools.jar"
+	};
+	
+	protected File getToolsJAR() {
+		List<File> jhomes = new ArrayList<>(2);
+		resolve(System.getenv("JAVA_HOME"), jhomes::add);
+		resolve(System.getProperty("java.home"), jhomes::add);
+		for (File jhome : jhomes) {
+			for (String tjPath : TOOLS_JAR_PATHS) {
+				File toolsJar = new File(jhome, tjPath);
+				if (toolsJar.isFile()) {
+					return toolsJar;
+				}
+			}
+		}
+		return null;
 	}
 	
+	private void resolve(String path, Consumer<File> requestor) {
+		if (path!=null) {
+			try {
+				File file = new File(path).getCanonicalFile();
+				if (file.exists()) {
+					requestor.accept(file);
+					return;
+				}
+			} catch (IOException e) {
+				//Ignore... this can happen because it tries to handle symbolic links
+			}
+		}
+	}
+	
+	private File getJavaHomeFromEnv() {
+		try {
+			File jhome = new File(System.getenv("JAVA_HOME"));
+			if (jhome!=null) {
+				jhome = jhome.getCanonicalFile();
+				if (jhome.isDirectory()) {
+					return jhome;
+				}
+			}
+		} catch (IOException e) {
+			//Ignore... this can happen because it tries to handle symbolic links
+		}
+		return null;
+	}
+
 	protected String getWorkingDirLocation() {
 		return System.getProperty("user.dir");
 	}