LLM agents increasingly draft messages on behalf of users, yet users routinely overshare sensitive information and disagree on what counts as private. Existing systems support only suppression (omitting sensitive information) and generalization (replacing information with an abstraction), and are typically evaluated on single isolated messages, leaving both the strategy space and evaluation setting incomplete. We formalize privacy-preserving LLM communication as an Information Sufficiency (IS) task, introduce free-text pseudonymization as a third strategy that replaces sensitive attributes with functionally equivalent alternatives, and propose a conversational evaluation protocol that assesses strategies under realistic multi-turn follow-up pressure. Across 792 scenarios spanning three power-relation types (institutional, peer, intimate) and three sensitivity categories (discrimination risk, social cost, boundary), we evaluate seven frontier LLMs on privacy at two granularities, covertness, and utility. Pseudonymization yields the strongest privacy\textendash utility tradeoff overall, and single-message evaluation systematically underestimates leakage, with generalization losing up to 16.3 percentage points of privacy under follow-up.
Figures & tables
Figure 1: Three privacy strategies applied to an LLM-drafted message. Suppression triggers follow-up; generalization partially reveals the domain; pseudonymization satisfies the receiver while protecting the true attribute.
Figure 2: Conversational evaluation protocol. Stage 1: strategy-conditioned reply; Stage 2: two rounds of non-adversarial follow-up; Stage 3: privacy, covertness, and utility evaluation on the full transcript.
HLS p ↓
Utility ↑
IS-AD p ↑
Model
None
Supp
Gen
Pseudo
None
Supp
Gen
Pseudo
None
Supp
Gen
Pseudo
Gemini 3.1 Pro
.40
.16
.29
.22
.99
.82
.72
.96
.61
.73
.57
.78
GLM-5
.30
.18
.25
.23
.93
.81
.79
.93
.68
.71
.64
.75
GPT-5.4
.30
.21
.27
.25
.96
.86
.85
.96
.69
.71
.65
.75
Kimi K2.5
.41
.17
.31
.24
.99
.77
.79
.97
.61
.68
.60
.76
MiniMax M2.1
.32
.22
.27
.30
.91
.82
.84
.90
.64
.68
.64
.66
Table 1: Main results (probed adversary evaluation). For each model we report three key metrics under four strategy conditions. Bold : best value per model per metric. ↓ : lower is better; ↑ : higher is better. Full per-metric breakdowns (EM p , CM p , Covertness) are in Appendix D .
Figure 4
Figure 4: Left: Privacy vs. covertness by model and strategy. Pseudonymization occupies the “high privacy, natural” quadrant. Right: Mean covertness by strategy. Pseudonymization matches the no-protection baseline.
Boundary
Discrim.
Social
Instit.
No Protection
0.727
0.490
0.823
Suppress
0.722
0.566
0.854
Generalize
0.629
0.452
0.776
Pseudonymize
0.761
0.617
0.762
N
2024
756
84
Peer
No Protection
0.695
0.696
0.721
Table 2: IS-AD p by social context. Each cell shows the mean IS-AD under probed adversary for four strategies. N = total conversations in that context across all strategies and models.
Appendix figures & tables7 assets
Supplementary material from the paper’s appendix.
Appendix
Model
Strategy
N
EM p ↓
CM p ↓
HLS p ↓
Util ↑
Covert ↑
MIL-AD p ↑
Gemini 3.1 Pro
No Protection
792
0.481
0.611
0.401
0.988
4.82
0.611
Suppress
792
0.161
0.256
0.163
0.823
3.67
0.732
Generalize
791
0.292
0.412
0.290
0.718
3.17
0.570
Pseudonymize
791
0.172
0.403
0.221
0.959
4.67
0.784
GLM-5
No Protection
792
0.326
0.451
0.298
0.929
4.22
0.676
Suppress
792
0.186
0.263
0.181
0.813
3.75
0.713
Appendix
Table 3: Full results under probed adversary evaluation. For each model we report all six metrics under four strategy conditions. Bold : best value per model per metric across all four strategies. ↓ : lower is better; ↑ : higher is better.
Model
No Prot
Suppress
Generalize
Pseudo
Gemini 3.1 Pro
+0.087
+0.095
+0.177
+0.047
GLM-5
+0.057
+0.093
+0.131
+0.032
GPT-5.4
+0.046
+0.094
+0.137
+0.074
Kimi K2.5
+0.096
+0.086
+0.158
+0.036
MiniMax M2.1
+0.091
+0.088
+0.123
+0.051
MiniMax M2.5
+0.027
+0.049
+0.041
+0.022
Appendix
Table 4: Vulnerability gap ( Δvuln = EM p − EM s ) showing how multi-turn probing increases exact match leakage.
Comparison
Gem 3.1 Pro
GLM-5
GPT-5.4
Kimi K2.5
MM M2.1
MM M2.5
Qwen3-8B
Pseudo vs No Prot
Δ
+0.173 ∗∗∗
+0.074 ∗∗∗
+0.057 ∗∗
+0.155 ∗∗∗
+0.020
+0.000
+0.016
r
0.50
0.25
0.19
0.46
0.06
0.01
0.06
Pseudo vs Suppress
Δ
+0.052 ∗∗∗
+0.037 ∗∗
+0.037 ∗∗
+0.082 ∗∗∗
− 0.020
+0.018 ∗
+0.035 ∗∗
r
0.21
0.15
0.15
0.28
0.04
0.13
0.17
Pseudo vs Gen
Δ
+0.213 ∗∗∗
+0.110 ∗∗∗
+0.093 ∗∗∗
+0.166 ∗∗∗
+0.015
+0.043 ∗∗∗
+0.065 ∗∗∗
r
0.57
0.36
0.32
0.45
0.06
0.23
0.29
Appendix
Table 5: Pairwise Wilcoxon signed-rank tests on MIL-AD p (scenario-paired). Δ : mean difference (A − B); r : effect size. ∗p<.05 , ∗∗p<.01 , ∗∗∗p<.001 .
Strategy
EM s
CM s
HLS s
MIL-AD s
No Protection
Mean
0.274
0.384
0.230
0.7545
Suppress
Mean
0.096
0.157
0.092
0.7948
Generalize
Mean
0.137
0.224
0.140
0.7491
Pseudonymize
Mean
0.152
0.302
0.168
0.8089
Appendix
Table 6: Results under the static adversary (single-message inference). Compare with Table 1 (probed) to see the ranking reversal for Suppress vs. Generalize.
Boundary
Discrim.
Social
Instit.
No Protection
0.706
0.478
0.807 ∗
Suppress
0.709
0.552
0.854 ∗
Generalize
0.618
0.441
0.776 ∗
Pseudonymize
0.745
0.615
0.714 ∗
N
2024
756
84
Peer
No Protection
0.683
0.691
0.712
Appendix
Table 7: MIL-AD p by social context. Each cell shows the mean MIL-AD under probed adversary for four strategies. N = total conversations in that context across all strategies and models.
Metric
α
HLS p
0.824
HLS s
0.872
Utility
0.606
IS-AD p
0.555
Appendix
Table 8: Inter-judge agreement (Krippendorff’s α , interval) across three LLM judges.
Aggregation
No Protect
Suppress
Generalize
Pseudo
MIL-AD (current)
0.6941
0.7304
0.6640
0.7642
Additive α=0.3
0.8782
0.8279
0.7933
0.8917
Additive α=0.5
0.8294
0.8301
0.7849
0.8609
Additive α=0.7
0.7805
0.8323
0.7765
0.8301
Harmonic mean
0.6941
0.7304
0.6640
0.7642
min(priv,util)
0.6653
0.6771
0.6075
0.7294
Appendix
Table 9: Strategy ranking under alternative privacy–utility aggregations. All metrics combine Privacy =1−HLSp and Utility. Bold marks the top-ranked strategy. Pseudonymize ranks first under 6 of 7 aggregations; the sole exception is when privacy is weighted at 70%, where Suppress leads by a negligible margin ( +0.002 ).