diff --git a/crates/formatter/src/internal/format/member_access.rs b/crates/formatter/src/internal/format/member_access.rs
index 8091a14d..bd5be6e8 100644
--- a/crates/formatter/src/internal/format/member_access.rs
+++ b/crates/formatter/src/internal/format/member_access.rs
@@ -314,7 +314,7 @@ impl<'arena> MemberAccessChain<'arena> {
             return true;
         }
 
-        if accesses_len <= 3 {
+        if accesses_len <= 3 && !f.in_condition {
             // we must have at least 2 breaks for chains of length 3 or less
             return false;
         }
@@ -581,9 +581,10 @@ pub(super) fn print_member_access_chain<'arena>(
     let mut last_element_end = member_access_chain.base.span().end;
     // Handle the first access
 
-    if should_inline_first_access(f, member_access_chain)
-        && let Some((_, first_chain_link)) = accesses_iter.next()
-    {
+    let should_inline = should_inline_first_access(f, member_access_chain)
+        || (f.in_condition && member_access_chain.accesses.len() <= 3);
+
+    if should_inline && let Some((_, first_chain_link)) = accesses_iter.next() {
         // Format the base object and first method call together
         parts.push(format_access_operator(
             f,
@@ -642,7 +643,11 @@ pub(super) fn print_member_access_chain<'arena>(
         }
 
         if must_break {
-            parts.push(Document::Indent(contents));
+            if f.in_condition {
+                parts.push(Document::Array(contents));
+            } else {
+                parts.push(Document::Indent(contents));
+            }
         } else {
             parts.push(Document::IndentIfBreak(IndentIfBreak::new(group_id, contents)));
         }
diff --git a/crates/formatter/tests/cases/if_multiline_operator/after.php b/crates/formatter/tests/cases/if_multiline_operator/after.php
new file mode 100644
index 00000000..8ff0b72c
--- /dev/null
+++ b/crates/formatter/tests/cases/if_multiline_operator/after.php
@@ -0,0 +1,47 @@
+<?php
+
+if (!$this->windows && !$this->getSession()
+    ->getDriver() instanceof BrowserKitDriver) {
+    if (!$this->getSession()->isStarted()) {
+        $this->getSession()->start();
+    }
+
+    $this->windows = $this->getSession()->getWindowNames();
+}
+
+if (!$this->windows && !$this
+    ->getSession()
+    ->getDriver()
+    ->exampleCall()
+    ->gimmeMore()
+    ->andAnother() instanceof BrowserKitDriver) {
+    if (!$this->getSession()->isStarted()) {
+        $this->getSession()->start();
+    }
+
+    $this->windows = $this->getSession()->getWindowNames();
+}
+
+if (
+    $node->bundle() == 'organization_profile'
+    && \Drupal::service('example_recruiter_verification.example_recruiter_verification_helper')
+        ->isRecruiterVerificationEnabled()
+) {
+    $a = $b;
+}
+
+if (
+    $node->bundle() == 'organization_profile'
+    && \Drupal::service('example_recruiter_verification.example_recruiter_verification_helper')
+        ->somePublicProperty
+) {
+    $a = $b;
+}
+
+if (
+    $node->bundle() == 'organization_profile'
+    && $object->method('example_recruiter_verification.example_recruiter_verification_helper')
+        ->somePublicProperty
+) {
+    $a = $b;
+}
diff --git a/crates/formatter/tests/cases/if_multiline_operator/before.php b/crates/formatter/tests/cases/if_multiline_operator/before.php
new file mode 100644
index 00000000..d9d4b4c8
--- /dev/null
+++ b/crates/formatter/tests/cases/if_multiline_operator/before.php
@@ -0,0 +1,38 @@
+<?php
+
+if (!$this->windows && !$this->getSession()
+    ->getDriver() instanceof BrowserKitDriver) {
+    if (!$this->getSession()->isStarted()) {
+        $this->getSession()->start();
+    }
+
+    $this->windows = $this->getSession()->getWindowNames();
+}
+
+if (!$this->windows && !$this
+    ->getSession()
+    ->getDriver()
+    ->exampleCall()
+    ->gimmeMore()
+    ->andAnother() instanceof BrowserKitDriver) {
+    if (!$this->getSession()->isStarted()) {
+        $this->getSession()->start();
+    }
+
+    $this->windows = $this->getSession()->getWindowNames();
+}
+
+if ($node->bundle() == 'organization_profile' && \Drupal::service('example_recruiter_verification.example_recruiter_verification_helper')
+    ->isRecruiterVerificationEnabled()) {
+    $a = $b;
+}
+
+if ($node->bundle() == 'organization_profile' && \Drupal::service('example_recruiter_verification.example_recruiter_verification_helper')
+    ->somePublicProperty) {
+    $a = $b;
+}
+
+if ($node->bundle() == 'organization_profile' && $object->method('example_recruiter_verification.example_recruiter_verification_helper')
+    ->somePublicProperty) {
+    $a = $b;
+}
diff --git a/crates/formatter/tests/cases/if_multiline_operator/settings.inc b/crates/formatter/tests/cases/if_multiline_operator/settings.inc
new file mode 100644
index 00000000..ac5c50ff
--- /dev/null
+++ b/crates/formatter/tests/cases/if_multiline_operator/settings.inc
@@ -0,0 +1,5 @@
+FormatSettings {
+  preserve_breaking_conditional_expression: true,
+  preserve_breaking_member_access_chain: true,
+  ..Default::default()
+}
diff --git a/crates/formatter/tests/mod.rs b/crates/formatter/tests/mod.rs
index b70e9c33..608f6265 100644
--- a/crates/formatter/tests/mod.rs
+++ b/crates/formatter/tests/mod.rs
@@ -237,6 +237,7 @@ test_case!(idempotent_chain_with_array);
 test_case!(match_idempotency);
 test_case!(heredoc_indentation);
 test_case!(heredoc_indentation_disabled);
+test_case!(if_multiline_operator);
 
 // A special test case for regressions in the Psl codebase
 test_case!(psl_regressions);