diff --git a/document-readers/pdf-reader/src/main/java/org/springframework/ai/reader/pdf/ParagraphPdfDocumentReader.java b/document-readers/pdf-reader/src/main/java/org/springframework/ai/reader/pdf/ParagraphPdfDocumentReader.java
index 6c7385474..1785c8325 100644
--- a/document-readers/pdf-reader/src/main/java/org/springframework/ai/reader/pdf/ParagraphPdfDocumentReader.java
+++ b/document-readers/pdf-reader/src/main/java/org/springframework/ai/reader/pdf/ParagraphPdfDocumentReader.java
@@ -110,6 +110,9 @@ public class ParagraphPdfDocumentReader implements DocumentReader {
 
 			this.resourceFileName = pdfResource.getFile();
 		}
+		catch (IllegalArgumentException iae) {
+			throw iae;
+		}
 		catch (Exception e) {
 			throw new RuntimeException(e);
 		}
diff --git a/document-readers/pdf-reader/src/main/java/org/springframework/ai/reader/pdf/config/ParagraphManager.java b/document-readers/pdf-reader/src/main/java/org/springframework/ai/reader/pdf/config/ParagraphManager.java
index 1ccf87466..d92d58d75 100644
--- a/document-readers/pdf-reader/src/main/java/org/springframework/ai/reader/pdf/config/ParagraphManager.java
+++ b/document-readers/pdf-reader/src/main/java/org/springframework/ai/reader/pdf/config/ParagraphManager.java
@@ -28,6 +28,7 @@ import org.apache.pdfbox.pdmodel.interactive.documentnavigation.destination.PDPa
 import org.apache.pdfbox.pdmodel.interactive.documentnavigation.outline.PDOutlineItem;
 import org.apache.pdfbox.pdmodel.interactive.documentnavigation.outline.PDOutlineNode;
 
+import org.springframework.util.Assert;
 import org.springframework.util.CollectionUtils;
 
 /**
@@ -75,6 +76,13 @@ public class ParagraphManager {
 	private final PDDocument document;
 
 	public ParagraphManager(PDDocument document) {
+
+		Assert.notNull(document, "PDDocument must not be null");
+		Assert.notNull(document.getDocumentCatalog().getDocumentOutline(),
+				"Document outline (e.g. TOC) is null. "
+						+ "Make sure the PDF document has a table of contents (TOC). If not, consider the "
+						+ "PagePdfDocumentReader or the TikaDocumentReader instead.");
+
 		try {
 
 			this.document = document;
diff --git a/document-readers/pdf-reader/src/test/java/org/springframework/ai/reader/pdf/ParagraphPdfDocumentReaderTests.java b/document-readers/pdf-reader/src/test/java/org/springframework/ai/reader/pdf/ParagraphPdfDocumentReaderTests.java
new file mode 100644
index 000000000..3d5ca379d
--- /dev/null
+++ b/document-readers/pdf-reader/src/test/java/org/springframework/ai/reader/pdf/ParagraphPdfDocumentReaderTests.java
@@ -0,0 +1,53 @@
+/*
+ * Copyright 2024-2024 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.ai.reader.pdf;
+
+import org.junit.jupiter.api.Test;
+
+import org.springframework.ai.reader.ExtractedTextFormatter;
+import org.springframework.ai.reader.pdf.config.PdfDocumentReaderConfig;
+
+import static org.assertj.core.api.Assertions.assertThatThrownBy;
+
+/**
+ * @author Christian Tzolov
+ */
+public class ParagraphPdfDocumentReaderTests {
+
+	@Test
+	public void testPdfWithoutToc() {
+
+		assertThatThrownBy(() -> {
+
+			new ParagraphPdfDocumentReader("classpath:/sample1.pdf",
+					PdfDocumentReaderConfig.builder()
+						.withPageTopMargin(0)
+						.withPageBottomMargin(0)
+						.withPageExtractedTextFormatter(ExtractedTextFormatter.builder()
+							.withNumberOfTopTextLinesToDelete(0)
+							.withNumberOfBottomTextLinesToDelete(3)
+							.withNumberOfTopPagesToSkipBeforeDelete(0)
+							.build())
+						.withPagesPerDocument(1)
+						.build());
+		}).isInstanceOf(IllegalArgumentException.class)
+			.hasMessageContaining(
+					"Document outline (e.g. TOC) is null. Make sure the PDF document has a table of contents (TOC). If not, consider the PagePdfDocumentReader or the TikaDocumentReader instead.");
+
+	}
+
+}