diff --git a/.chloggen/pkg-stanza-recombine-overwrite-with-2.yaml b/.chloggen/pkg-stanza-recombine-overwrite-with-2.yaml
new file mode 100755
index 000000000000..ac63aa545c75
--- /dev/null
+++ b/.chloggen/pkg-stanza-recombine-overwrite-with-2.yaml
@@ -0,0 +1,32 @@
+# Use this changelog template to create an entry for release notes.
+
+# One of 'breaking', 'deprecation', 'new_component', 'enhancement', 'bug_fix'
+change_type: breaking
+
+# The name of the component, or a single word describing the area of concern, (e.g. filelogreceiver)
+component: pkg/stanza
+
+# A brief description of the change.  Surround your text with quotes ("") if it needs to start with a backtick (`).
+note: Invert recombine operator's 'overwrite_with' default value.
+
+# Mandatory: One or more tracking issues related to the change. You can use the PR number here if no issue exists.
+issues: [30783]
+
+# (Optional) One or more lines of additional information to render under the primary note.
+# These lines will be padded with 2 spaces and then inserted directly into the document.
+# Use pipe (|) for multiline entries.
+subtext: |
+    Previously, the default value was `oldest`, meaning that the recombine operator _should_ emit the
+    first entry from each batch (with the recombined field). However, the actual behavior was inverted.
+    This fixes the bug but also inverts the default setting so as to effectively cancel out the bug fix
+    for users who were not using this setting. For users who were explicitly setting `overwrite_with`,
+    this corrects the intended behavior.
+
+# If your change doesn't affect end users or the exported elements of any package,
+# you should instead start your pull request title with [chore] or use the "Skip Changelog" label.
+# Optional: The change log or logs in which this entry should be included.
+# e.g. '[user]' or '[user, api]'
+# Include 'user' if the change is relevant to end users.
+# Include 'api' if there is a change to a library API.
+# Default: '[user]'
+change_logs: []
diff --git a/.chloggen/pkg-stanza-recombine-overwrite-with.yaml b/.chloggen/pkg-stanza-recombine-overwrite-with.yaml
new file mode 100755
index 000000000000..13c56cc519e4
--- /dev/null
+++ b/.chloggen/pkg-stanza-recombine-overwrite-with.yaml
@@ -0,0 +1,27 @@
+# Use this changelog template to create an entry for release notes.
+
+# One of 'breaking', 'deprecation', 'new_component', 'enhancement', 'bug_fix'
+change_type: bug_fix
+
+# The name of the component, or a single word describing the area of concern, (e.g. filelogreceiver)
+component: pkg/stanza
+
+# A brief description of the change.  Surround your text with quotes ("") if it needs to start with a backtick (`).
+note: Fix bug where recombine operator's 'overwrite_with' condition was inverted.
+
+# Mandatory: One or more tracking issues related to the change. You can use the PR number here if no issue exists.
+issues: [30783]
+
+# (Optional) One or more lines of additional information to render under the primary note.
+# These lines will be padded with 2 spaces and then inserted directly into the document.
+# Use pipe (|) for multiline entries.
+subtext:
+
+# If your change doesn't affect end users or the exported elements of any package,
+# you should instead start your pull request title with [chore] or use the "Skip Changelog" label.
+# Optional: The change log or logs in which this entry should be included.
+# e.g. '[user]' or '[user, api]'
+# Include 'user' if the change is relevant to end users.
+# Include 'api' if there is a change to a library API.
+# Default: '[user]'
+change_logs: []
diff --git a/pkg/stanza/operator/transformer/recombine/recombine.go b/pkg/stanza/operator/transformer/recombine/recombine.go
index 0a67d7fe4a82..ffdf86897a9a 100644
--- a/pkg/stanza/operator/transformer/recombine/recombine.go
+++ b/pkg/stanza/operator/transformer/recombine/recombine.go
@@ -40,7 +40,7 @@ func NewConfigWithID(operatorID string) *Config {
 		MaxBatchSize:      1000,
 		MaxSources:        1000,
 		CombineWith:       defaultCombineWith,
-		OverwriteWith:     "oldest",
+		OverwriteWith:     "newest",
 		ForceFlushTimeout: 5 * time.Second,
 		SourceIdentifier:  entry.NewAttributeField("file.path"),
 	}
@@ -344,9 +344,9 @@ func (r *Transformer) flushSource(source string, deleteSource bool) error {
 	entries := batch.entries
 
 	if r.overwriteWithOldest {
-		base = entries[0]
-	} else {
 		base = entries[len(entries)-1]
+	} else {
+		base = entries[0]
 	}
 
 	// Set the recombined field on the entry
diff --git a/pkg/stanza/operator/transformer/recombine/recombine_test.go b/pkg/stanza/operator/transformer/recombine/recombine_test.go
index 9887d28cc537..90bb29a47abe 100644
--- a/pkg/stanza/operator/transformer/recombine/recombine_test.go
+++ b/pkg/stanza/operator/transformer/recombine/recombine_test.go
@@ -127,6 +127,25 @@ func TestTransformer(t *testing.T) {
 				entryWithBody(t2, "test2"),
 				entryWithBody(t2, "test1"),
 			},
+			[]*entry.Entry{
+				entryWithBody(t1, "test1\ntest2"),
+			},
+		},
+		{
+			"ThreeEntriesFirstOldest",
+			func() *Config {
+				cfg := NewConfig()
+				cfg.CombineField = entry.NewBodyField()
+				cfg.IsFirstEntry = "body == 'test1'"
+				cfg.OutputIDs = []string{"fake"}
+				cfg.OverwriteWith = "oldest"
+				return cfg
+			}(),
+			[]*entry.Entry{
+				entryWithBody(t1, "test1"),
+				entryWithBody(t2, "test2"),
+				entryWithBody(t2, "test1"),
+			},
 			[]*entry.Entry{
 				entryWithBody(t2, "test1\ntest2"),
 			},
@@ -159,7 +178,7 @@ func TestTransformer(t *testing.T) {
 				cfg.CombineField = entry.NewBodyField()
 				cfg.IsFirstEntry = "body == 'file1'"
 				cfg.OutputIDs = []string{"fake"}
-				cfg.OverwriteWith = "newest"
+				cfg.OverwriteWith = "oldest"
 				return cfg
 			}(),
 			[]*entry.Entry{
@@ -267,7 +286,7 @@ func TestTransformer(t *testing.T) {
 				cfg.CombineField = entry.NewBodyField("message")
 				cfg.CombineWith = ""
 				cfg.IsLastEntry = "body.logtag == 'F'"
-				cfg.OverwriteWith = "newest"
+				cfg.OverwriteWith = "oldest"
 				cfg.ForceFlushTimeout = 100 * time.Millisecond
 				cfg.OutputIDs = []string{"fake"}
 				return cfg