diff --git a/src/main/java/com/hubspot/jinjava/tree/parse/StringTokenScanner.java b/src/main/java/com/hubspot/jinjava/tree/parse/StringTokenScanner.java
index 0e5df631c..6ec9dd259 100644
--- a/src/main/java/com/hubspot/jinjava/tree/parse/StringTokenScanner.java
+++ b/src/main/java/com/hubspot/jinjava/tree/parse/StringTokenScanner.java
@@ -608,11 +608,14 @@ private Token emitToken(int kind) {
       (t instanceof TagToken || t instanceof NoteToken) &&
       config.isTrimBlocks() &&
       currPost < length &&
-      is[currPost] == '\n'
+      (is[currPost] == '\n' ||
+        (is[currPost] == '\r' && currPost + 1 < length && is[currPost + 1] == '\n'))
     ) {
-      lastNewlinePos = currPost + 1;
-      ++currPost;
-      ++tokenStart;
+      int newlineLength = is[currPost] == '\r' ? 2 : 1;
+      currPost += newlineLength;
+      tokenStart += newlineLength;
+      lastNewlinePos = currPost;
+      ++currLine;
     }
 
     if (t instanceof TagToken) {
diff --git a/src/main/java/com/hubspot/jinjava/tree/parse/TokenScanner.java b/src/main/java/com/hubspot/jinjava/tree/parse/TokenScanner.java
index de3b6e040..e35a87a21 100644
--- a/src/main/java/com/hubspot/jinjava/tree/parse/TokenScanner.java
+++ b/src/main/java/com/hubspot/jinjava/tree/parse/TokenScanner.java
@@ -287,11 +287,14 @@ private Token newToken(int kind) {
       (t instanceof TagToken || t instanceof NoteToken) &&
       config.isTrimBlocks() &&
       currPost < length &&
-      is[currPost] == '\n'
+      (is[currPost] == '\n' ||
+        (is[currPost] == '\r' && currPost + 1 < length && is[currPost + 1] == '\n'))
     ) {
+      int newlineLength = is[currPost] == '\r' ? 2 : 1;
+      currPost += newlineLength;
+      tokenStart += newlineLength;
       lastNewlinePos = currPost;
-      ++currPost;
-      ++tokenStart;
+      ++currLine;
     }
 
     if (t instanceof TagToken) {
diff --git a/src/test/java/com/hubspot/jinjava/tree/TreeParserTest.java b/src/test/java/com/hubspot/jinjava/tree/TreeParserTest.java
index 7beba0733..4e5fb32ef 100644
--- a/src/test/java/com/hubspot/jinjava/tree/TreeParserTest.java
+++ b/src/test/java/com/hubspot/jinjava/tree/TreeParserTest.java
@@ -150,6 +150,41 @@ public void trimAndLstripBlocks() {
       .isEqualTo("<div>\n" + "        yay\n" + "</div>\n");
   }
 
+  @Test
+  public void itTrimsCrLfAfterBlocks() {
+    interpreter =
+      new Jinjava(
+        BaseJinjavaTest
+          .newConfigBuilder()
+          .withLstripBlocks(true)
+          .withTrimBlocks(true)
+          .build()
+      )
+        .newInterpreter();
+    interpreter.getContext().put("bootefiDev", "sda");
+    interpreter.getContext().put("bootDev", "sda");
+    interpreter.getContext().put("rootDev", "sda");
+
+    String template =
+      "{% if bootefiDev %}\r\n" +
+      "part /boot/efi --fstype=\"efi\" --size=500 --ondisk={{ bootefiDev }}\r\n" +
+      "{% endif %}\r\n" +
+      "{% if bootDev %}\r\n" +
+      "part /boot --fstype ext4 --size=2048 --ondisk={{ bootDev }}\r\n" +
+      "{% endif %}\r\n" +
+      "{% if rootDev %}\r\n" +
+      "part / --fstype ext4 --size=1 --grow  --ondisk={{ rootDev }}\r\n" +
+      "{% endif %}\r\n";
+
+    assertThat(interpreter.render(interpreter.parse(template)))
+      .isEqualTo(
+        "part /boot/efi --fstype=\"efi\" --size=500 --ondisk=sda\r\n" +
+        "part /boot --fstype ext4 --size=2048 --ondisk=sda\r\n" +
+        "part / --fstype ext4 --size=1 --grow  --ondisk=sda\r\n"
+      );
+    assertThat(interpreter.getErrors()).isEmpty();
+  }
+
   @Test
   public void trimAndLstripCommentBlocks() {
     interpreter =
diff --git a/src/test/java/com/hubspot/jinjava/tree/parse/StringTokenScannerSymbolsTest.java b/src/test/java/com/hubspot/jinjava/tree/parse/StringTokenScannerSymbolsTest.java
index b7af6c074..c65851b23 100644
--- a/src/test/java/com/hubspot/jinjava/tree/parse/StringTokenScannerSymbolsTest.java
+++ b/src/test/java/com/hubspot/jinjava/tree/parse/StringTokenScannerSymbolsTest.java
@@ -323,6 +323,59 @@ public void itRespectsLstripBlocksWithLatexSymbols() {
     assertThat(result).isEqualTo("hello\n");
   }
 
+  @Test
+  public void itRespectsWhitespaceOptionsWithCrLfAndAngleSymbols() {
+    assertCrLfWhitespaceOptions(
+      ANGLE_SYMBOLS,
+      "    <% if show %>\r\nhello\r\n    <% endif %>\r\ntail"
+    );
+  }
+
+  @Test
+  public void itRespectsWhitespaceOptionsWithCrLfAndLatexSymbols() {
+    assertCrLfWhitespaceOptions(
+      LATEX_SYMBOLS,
+      "    \\BLOCK{ if show }\r\nhello\r\n    \\BLOCK{ endif }\r\ntail"
+    );
+  }
+
+  @Test
+  public void itTrimsCrLfAroundCommentsAndRawBlocksWithCustomSymbols() {
+    for (StringTokenScannerSymbols symbols : Lists.newArrayList(
+      ANGLE_SYMBOLS,
+      LATEX_SYMBOLS
+    )) {
+      Jinjava j = new Jinjava(
+        BaseJinjavaTest
+          .newConfigBuilder()
+          .withTokenScannerSymbols(symbols)
+          .withTrimBlocks(true)
+          .withKeepTrailingNewline(true)
+          .build()
+      );
+      String expression =
+        symbols.getExpressionStart() + " value " + symbols.getExpressionEnd();
+      String template =
+        symbols.getOpeningComment() +
+        " comment " +
+        symbols.getClosingComment() +
+        "\r\n" +
+        symbols.getExpressionStartWithTag() +
+        " raw " +
+        symbols.getExpressionEndWithTag() +
+        "\r\n" +
+        expression +
+        "\r\n" +
+        symbols.getExpressionStartWithTag() +
+        " endraw " +
+        symbols.getExpressionEndWithTag() +
+        "\r\ntail";
+
+      assertThat(j.render(template, ImmutableMap.of("value", "evaluated")))
+        .isEqualTo(expression + "\r\ntail");
+    }
+  }
+
   @Test
   public void builderRejectsEmptyDelimiter() {
     assertThatThrownBy(() ->
@@ -505,6 +558,31 @@ public void itHandlesBothLinePrefixesTogether() {
 
   // ── Helper ────────────────────────────────────────────────────────────────
 
+  private void assertCrLfWhitespaceOptions(
+    StringTokenScannerSymbols symbols,
+    String template
+  ) {
+    for (boolean trimBlocks : new boolean[] { false, true }) {
+      for (boolean lstripBlocks : new boolean[] { false, true }) {
+        Jinjava j = new Jinjava(
+          BaseJinjavaTest
+            .newConfigBuilder()
+            .withTokenScannerSymbols(symbols)
+            .withTrimBlocks(trimBlocks)
+            .withLstripBlocks(lstripBlocks)
+            .withKeepTrailingNewline(true)
+            .build()
+        );
+        String indent = lstripBlocks ? "" : "    ";
+        String tagNewline = trimBlocks ? "" : "\r\n";
+
+        assertThat(j.render(template, ImmutableMap.of("show", true)))
+          .as("trimBlocks=%s, lstripBlocks=%s", trimBlocks, lstripBlocks)
+          .isEqualTo(indent + tagNewline + "hello\r\n" + indent + tagNewline + "tail");
+      }
+    }
+  }
+
   private Jinjava jinjavaWith(StringTokenScannerSymbols symbols) {
     return new Jinjava(
       BaseJinjavaTest
diff --git a/src/test/java/com/hubspot/jinjava/tree/parse/TokenWhitespaceTest.java b/src/test/java/com/hubspot/jinjava/tree/parse/TokenWhitespaceTest.java
index 09c0f643a..367cae17c 100644
--- a/src/test/java/com/hubspot/jinjava/tree/parse/TokenWhitespaceTest.java
+++ b/src/test/java/com/hubspot/jinjava/tree/parse/TokenWhitespaceTest.java
@@ -9,6 +9,7 @@
 import java.io.IOException;
 import java.nio.charset.StandardCharsets;
 import java.util.List;
+import java.util.stream.Collectors;
 import org.junit.Test;
 
 public class TokenWhitespaceTest {
@@ -32,6 +33,99 @@ public void trimBlocksTrimsAfterCommentTag() {
     assertThat(tokens.get(4).getImage()).isEqualTo("        whoop\n</div>\n");
   }
 
+  @Test
+  public void trimBlocksTracksTheNextTokenPosition() {
+    for (String block : List.of("{% set x = 1 %}", "{# comment #}")) {
+      for (String newline : List.of("\n", "\r\n")) {
+        for (List<Token> tokens : scanBoth(block + newline + "  {{ x }}", true)) {
+          assertThat(tokens)
+            .extracting(Token::getImage)
+            .containsExactly(block, "  ", "{{ x }}");
+          assertThat(tokens.get(0).getLineNumber()).isEqualTo(1);
+          assertThat(tokens.get(2).getLineNumber()).isEqualTo(2);
+          assertThat(tokens.get(2).getStartPosition()).isEqualTo(3);
+        }
+      }
+    }
+  }
+
+  @Test
+  public void trimBlocksConsumesOnlyOneNewline() {
+    for (String block : List.of("{% set x = 1 %}", "{# comment #}")) {
+      for (String first : List.of("\n", "\r\n")) {
+        for (String second : List.of("\n", "\r\n")) {
+          for (List<Token> tokens : scanBoth(block + first + second + "{{ x }}", true)) {
+            assertThat(tokens)
+              .extracting(Token::getImage)
+              .containsExactly(block, second, "{{ x }}");
+            assertThat(tokens.get(2).getLineNumber()).isEqualTo(3);
+            assertThat(tokens.get(2).getStartPosition()).isEqualTo(1);
+          }
+        }
+      }
+    }
+  }
+
+  @Test
+  public void trimBlocksHandlesNewlinesAtEndOfInput() {
+    for (String block : List.of("{% set x = 1 %}", "{# comment #}")) {
+      for (String newline : List.of("\n", "\r\n")) {
+        for (List<Token> tokens : scanBoth(block + newline, true)) {
+          assertThat(tokens).extracting(Token::getImage).containsExactly(block);
+        }
+      }
+    }
+  }
+
+  @Test
+  public void trimBlocksPreservesStandaloneCarriageReturnsAndInterveningWhitespace() {
+    for (String block : List.of("{% set x = 1 %}", "{# comment #}")) {
+      for (String suffix : List.of("", "\r", "\rtext", " \r\n", "\t\n", "\r\r\n")) {
+        String input = block + suffix;
+        for (List<Token> tokens : scanBoth(input, true)) {
+          assertThat(tokens.stream().map(Token::getImage).collect(Collectors.joining()))
+            .isEqualTo(input);
+        }
+      }
+    }
+  }
+
+  @Test
+  public void trimBlocksDoesNotTrimAfterExpressions() {
+    for (String newline : List.of("\n", "\r\n")) {
+      String input = "{{ 1 }}" + newline + "text";
+      for (List<Token> tokens : scanBoth(input, true)) {
+        assertThat(tokens)
+          .extracting(Token::getImage)
+          .containsExactly("{{ 1 }}", newline + "text");
+      }
+    }
+  }
+
+  @Test
+  public void disabledTrimBlocksPreservesNewlines() {
+    for (String block : List.of("{% set x = 1 %}", "{# comment #}")) {
+      for (String newline : List.of("\n", "\r\n")) {
+        for (List<Token> tokens : scanBoth(block + newline + "text", false)) {
+          assertThat(tokens)
+            .extracting(Token::getImage)
+            .containsExactly(block, newline + "text");
+        }
+      }
+    }
+  }
+
+  private List<List<Token>> scanBoth(String input, boolean trimBlocks) {
+    JinjavaConfig config = BaseJinjavaTest
+      .newConfigBuilder()
+      .withTrimBlocks(trimBlocks)
+      .build();
+    return List.of(
+      Lists.newArrayList(new TokenScanner(input, config)),
+      Lists.newArrayList(new StringTokenScanner(input, config))
+    );
+  }
+
   private List<Token> scanTokens(String srcPath, JinjavaConfig config) {
     try {
       return Lists.newArrayList(