diff --git a/pkg/jobs/execution_detail_utils.go b/pkg/jobs/execution_detail_utils.go
index 46a7c3121341..b1a13bb5ff81 100644
--- a/pkg/jobs/execution_detail_utils.go
+++ b/pkg/jobs/execution_detail_utils.go
@@ -60,6 +60,9 @@ func WriteProtobinExecutionDetailFile(
 // `~profiler/` prefix. Files written using this method can be read using the
 // `ReadExecutionDetailFile` and will show up in the list of files displayed on
 // the jobs' Advanced Debugging DBConsole page.
+//
+// This method clears any existing file with the same filename before writing a
+// new one.
 func WriteExecutionDetailFile(
 	ctx context.Context, filename string, data []byte, txn isql.Txn, jobID jobspb.JobID,
 ) error {
diff --git a/pkg/jobs/job_info_utils.go b/pkg/jobs/job_info_utils.go
index 60c059125c6b..9420ed324601 100644
--- a/pkg/jobs/job_info_utils.go
+++ b/pkg/jobs/job_info_utils.go
@@ -27,12 +27,22 @@ const bundleChunkSize = 1 << 20 // 1 MiB
 const finalChunkSuffix = "#_final"
 
 // WriteChunkedFileToJobInfo will break up data into chunks of a fixed size, and
-// gzip compress them before writing them to the job_info table
+// gzip compress them before writing them to the job_info table. This method
+// clears any existing chunks with the same filename before writing the new
+// chunks and so if the caller wishes to preserve history they must use a
+// unique filename.
 func WriteChunkedFileToJobInfo(
 	ctx context.Context, filename string, data []byte, txn isql.Txn, jobID jobspb.JobID,
 ) error {
+	finalChunkName := filename + finalChunkSuffix
 	jobInfo := InfoStorageForJob(txn, jobID)
 
+	// Clear any existing chunks with the same filename before writing new chunks.
+	// We clear all rows that with info keys in [filename, filename#_final~).
+	if err := jobInfo.DeleteRange(ctx, filename, finalChunkName+"~"); err != nil {
+		return err
+	}
+
 	var chunkCounter int
 	var chunkName string
 	for len(data) > 0 {
@@ -46,7 +56,7 @@ func WriteChunkedFileToJobInfo(
 			chunk = chunk[:chunkSize]
 		} else {
 			// This is the last chunk we will write, assign it a sentinel file name.
-			chunkName = filename + finalChunkSuffix
+			chunkName = finalChunkName
 		}
 		data = data[len(chunk):]
 		var err error
diff --git a/pkg/jobs/job_info_utils_test.go b/pkg/jobs/job_info_utils_test.go
index e66b35d730a6..f16c6a40ba92 100644
--- a/pkg/jobs/job_info_utils_test.go
+++ b/pkg/jobs/job_info_utils_test.go
@@ -55,6 +55,10 @@ func TestReadWriteChunkedFileToJobInfo(t *testing.T) {
 			name: "file greater than 1MiB",
 			data: make([]byte, 1<<20+1), // 1 MiB + 1 byte
 		},
+		{
+			name: "file much greater than 1MiB",
+			data: make([]byte, 10<<20), // 10 MiB
+		},
 	}
 
 	db := s.InternalDB().(isql.DB)
@@ -78,3 +82,95 @@ func TestReadWriteChunkedFileToJobInfo(t *testing.T) {
 		})
 	}
 }
+
+func TestOverwriteChunkingWithVariableLengths(t *testing.T) {
+	defer leaktest.AfterTest(t)()
+	defer log.Scope(t).Close(t)
+
+	rng, _ := randutil.NewTestRand()
+	ctx := context.Background()
+	params := base.TestServerArgs{}
+	params.Knobs.JobsTestingKnobs = NewTestingKnobsWithShortIntervals()
+	s := serverutils.StartServerOnly(t, params)
+	defer s.Stopper().Stop(ctx)
+
+	tests := []struct {
+		name       string
+		numChunks  int
+		data       []byte
+		moreChunks []byte
+		lessChunks []byte
+	}{
+		{
+			name:      "zero chunks",
+			data:      []byte{},
+			numChunks: 0,
+		},
+		{
+			name:      "one chunk",
+			numChunks: 1,
+		},
+		{
+			name:      "two chunks",
+			numChunks: 2,
+		},
+		{
+			name:      "five chunks",
+			numChunks: 5,
+		},
+	}
+
+	db := s.InternalDB().(isql.DB)
+	generateData := func(numChunks int) []byte {
+		data := make([]byte, (1<<20)*numChunks)
+		if len(data) > 0 {
+			randutil.ReadTestdataBytes(rng, data)
+		}
+		return data
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			tt.data = generateData(tt.numChunks)
+			// Write the first file, this will generate a certain number of chunks.
+			require.NoError(t, db.Txn(ctx, func(ctx context.Context, txn isql.Txn) error {
+				return WriteChunkedFileToJobInfo(ctx, tt.name, tt.data, txn, jobspb.JobID(123))
+			}))
+
+			// Overwrite the file with fewer chunks, this should delete the extra
+			// chunks before writing the new ones.
+			t.Run("overwrite with fewer chunks", func(t *testing.T) {
+				lessChunks := tt.numChunks - 1
+				if lessChunks >= 0 {
+					tt.data = generateData(lessChunks)
+					var got []byte
+					require.NoError(t, db.Txn(ctx, func(ctx context.Context, txn isql.Txn) error {
+						err := WriteChunkedFileToJobInfo(ctx, tt.name, tt.data, txn, jobspb.JobID(123))
+						if err != nil {
+							return err
+						}
+						got, err = ReadChunkedFileToJobInfo(ctx, tt.name, txn, jobspb.JobID(123))
+						return err
+					}))
+					require.Equal(t, tt.data, got)
+				}
+			})
+
+			// Overwrite the file with more chunks, this should delete the extra
+			// chunks before writing the new ones.
+			t.Run("overwrite with more chunks", func(t *testing.T) {
+				moreChunks := tt.numChunks + 1
+				tt.data = generateData(moreChunks)
+				var got []byte
+				require.NoError(t, db.Txn(ctx, func(ctx context.Context, txn isql.Txn) error {
+					err := WriteChunkedFileToJobInfo(ctx, tt.name, tt.data, txn, jobspb.JobID(123))
+					if err != nil {
+						return err
+					}
+					got, err = ReadChunkedFileToJobInfo(ctx, tt.name, txn, jobspb.JobID(123))
+					return err
+				}))
+				require.Equal(t, tt.data, got)
+			})
+		})
+	}
+}