diff --git a/cmd/entire/cli/strategy/manual_commit_condensation.go b/cmd/entire/cli/strategy/manual_commit_condensation.go
index 3546868354..b78594c542 100644
--- a/cmd/entire/cli/strategy/manual_commit_condensation.go
+++ b/cmd/entire/cli/strategy/manual_commit_condensation.go
@@ -213,7 +213,7 @@ func prepareTranscriptForStorage(
 	return externalized, assets, int64(len(sanitized))
 }
 
-// prepareTaskTranscriptForStorage runs the sanitize -> externalize -> redact
+// prepareTaskTranscriptForStorage runs the sanitize -> externalize -> cap -> redact
 // chain for a single subagent transcript, mirroring prepareTranscriptForStorage's
 // first two steps and then completing with the same redaction the session
 // transcript gets (see redactSessionTranscript). It is a SEPARATE entry point
@@ -228,10 +228,11 @@ func prepareTranscriptForStorage(
 //
 // It also carries checkpoint.prepareSubagentTranscript's size guard, for the
 // same reason: agent-<agent-id>.jsonl is neither chunked nor capped, and
-// redaction runs at roughly 220ms/MB. The cap is measured against the SANITIZED
-// bytes, not the raw ones — sanitizing strips the bulk (Codex encrypted_content
-// runs to ~20% of a rollout's bytes), so measuring raw would drop a transcript
-// oversized only by payloads about to be discarded.
+// redaction runs at roughly 220ms/MB. The cap is measured against the
+// EXTERNALIZED bytes (after sanitization and image extraction). This ensures
+// that a transcript which is only large because of inline images can still be
+// stored if those images are externalized into separate assets, while still
+// protecting the metadata branch from oversized text blobs.
 func prepareTaskTranscriptForStorage(
 	ctx, logCtx context.Context,
 	ag agent.Agent,
@@ -240,16 +241,22 @@ func prepareTaskTranscriptForStorage(
 	raw []byte,
 ) (redacted redact.RedactedBytes, assets []cpkg.TranscriptAsset, tooLarge bool, err error) {
 	sanitized := agent.SanitizeTranscriptForStorage(ag, raw)
-	if len(sanitized) > agent.MaxChunkSize {
+	externalized, assets := externalizeSessionImages(ctx, logCtx, state, sanitized)
+
+	// cap measures the size of the transcript that will be stored in git (after
+	// sanitization and image externalization, but before redaction). Oversized
+	// transcripts are dropped to keep the metadata branch pushable.
+	if len(externalized) > agent.MaxChunkSize {
 		logging.Warn(logCtx, "subagent transcript exceeds the blob size cap; storing task without it",
 			slog.String("session_id", state.SessionID),
 			slog.String("path", path),
 			slog.Int("raw_bytes", len(raw)),
 			slog.Int("sanitized_bytes", len(sanitized)),
+			slog.Int("externalized_bytes", len(externalized)),
 			slog.Int("cap", agent.MaxChunkSize))
 		return redact.RedactedBytes{}, nil, true, nil
 	}
-	externalized, assets := externalizeSessionImages(ctx, logCtx, state, sanitized)
+
 	redacted, _, err = redactSessionTranscript(logCtx, externalized)
 	if err != nil {
 		return redact.RedactedBytes{}, nil, false, err
diff --git a/cmd/entire/cli/strategy/manual_commit_condensation_test.go b/cmd/entire/cli/strategy/manual_commit_condensation_test.go
index dd28f20915..f7aee853ad 100644
--- a/cmd/entire/cli/strategy/manual_commit_condensation_test.go
+++ b/cmd/entire/cli/strategy/manual_commit_condensation_test.go
@@ -2,6 +2,7 @@ package strategy
 
 import (
 	"context"
+	"encoding/base64"
 	"encoding/json"
 	"os"
 	"os/exec"
@@ -1188,3 +1189,100 @@ func TestCheckpointStepCount(t *testing.T) {
 		})
 	}
 }
+
+// TestCondenseSession_TaskRecordImageExternalizationBoundary verifies the fix
+// for #2063: a task transcript whose RAW size (including base64 images) exceeds
+// the cap, but whose EXTERNALIZED size is within the cap, must be stored
+// successfully.
+func TestCondenseSession_TaskRecordImageExternalizationBoundary(t *testing.T) {
+	sessionID := "2026-08-23-task-image-boundary"
+	repo, state := setupCondensableSessionWithTranscript(t, sessionID)
+	// Enable image externalization for the test via env.
+	t.Setenv("ENTIRE_EXTERNALIZE_IMAGES", "1")
+	state.AgentType = agent.AgentTypeClaudeCode
+	dir := t.TempDir()
+	agentTranscriptPath := filepath.Join(dir, "agent-transcript.jsonl")
+
+	// Helper to write a transcript with a base64 image of specified decoded size.
+	writeImageTranscript := func(path string, decodedSize int) {
+		f, err := os.Create(path)
+		require.NoError(t, err)
+		defer f.Close()
+
+		_, err = f.WriteString(`{"role":"assistant","content":[{"type":"image","source":{"type":"base64","media_type":"image/png","data":"`)
+		require.NoError(t, err)
+
+		// Stream base64 to avoid huge memory allocations.
+		// 3 bytes -> 4 base64 chars.
+		buf := make([]byte, 3072) // multiple of 3
+		for i := 0; i < decodedSize; i += len(buf) {
+			n := len(buf)
+			if i+n > decodedSize {
+				n = decodedSize - i
+			}
+			for j := 0; j < n; j++ {
+				buf[j] = byte((i + j) % 256)
+			}
+			_, err = f.WriteString(base64.StdEncoding.EncodeToString(buf[:n]))
+			require.NoError(t, err)
+		}
+
+		_, err = f.WriteString(`"}}],"message":{"id":"msg_123"}}` + "\n")
+		require.NoError(t, err)
+	}
+
+	// Use small test boundaries to avoid huge disk writes.
+	// We use the imageextract package's internal variable.
+	// Since we are in the strategy package, we need to export it or use the real cap.
+	// Given the constraints, we will stick to the real 40MiB size for the primary test
+	// but add a comment explaining why we aren't using a smaller mock.
+	//
+	// Note: Case 1 already uses 40MiB which is > 32MiB (approx base64 for 50MiB)
+	// but < 50MiB. Actually, 40MiB decoded -> 53.3MiB base64, which is > 50MiB cap.
+	// The goal is to prove that after externalization (placeholder only), it's < 50MiB.
+
+	// Case 1: 40 MiB decoded -> ~53.3 MiB base64.
+	// This exceeds agent.MaxChunkSize (50 MiB) in raw form.
+	// After externalization, the transcript will only contain a placeholder.
+	writeImageTranscript(agentTranscriptPath, 40*1024*1024)
+
+	state.TaskRecords = []session.TaskRecord{
+		{
+			ToolUseID:              "toolu_boundary",
+			AgentID:                "agent-boundary",
+			DeclaredTranscriptPath: agentTranscriptPath,
+			CompletedAt:            time.Now(),
+		},
+	}
+	require.NoError(t, SaveSessionState(context.Background(), state))
+	checkpointID := id.MustCheckpointID("aabbccdd2063")
+	result, err := (&ManualCommitStrategy{}).CondenseSession(context.Background(), repo, checkpointID, state, nil)
+	require.NoError(t, err)
+	require.False(t, result.Skipped)
+
+	// Verify the transcript was stored.
+	jsonl, ok := checkpointTaskFile(t, repo, checkpointID, "tasks/toolu_boundary/agent-agent-boundary.jsonl")
+	require.True(t, ok, "transcript must be stored because externalized size is under cap")
+	require.Contains(t, jsonl, "entire-asset:assets/", "transcript must contain the asset placeholder")
+	require.Less(t, len(jsonl), 1024, "transcript must be shrunken")
+
+	// Case 2: Image that is NOT externalized and hits the 50MiB cap.
+	// Since we can't easily mock agent.MaxChunkSize (it's a const),
+	// we use a 51MiB image. Because it's > 50MiB DECODED, it stays inline
+	// and then prepareTaskTranscriptForStorage hits the MaxChunkSize cap.
+	writeImageTranscript(agentTranscriptPath, 51*1024*1024)
+
+	state.TaskRecords[0].ToolUseID = "toolu_oversize"
+	checkpointID2 := id.MustCheckpointID("aabbccdd2064")
+	_, err = (&ManualCommitStrategy{}).CondenseSession(context.Background(), repo, checkpointID2, state, nil)
+	require.NoError(t, err)
+
+	taskJSON, ok := checkpointTaskFile(t, repo, checkpointID2, "tasks/toolu_oversize/task.json")
+	require.True(t, ok)
+	var meta struct {
+		TranscriptUnavailableReason string `json:"transcript_unavailable_reason"`
+	}
+	require.NoError(t, json.Unmarshal([]byte(taskJSON), &meta))
+	require.Equal(t, taskTranscriptReasonTooLarge, meta.TranscriptUnavailableReason,
+		"transcript with >50MiB decoded image must hit the cap")
+}