OPINION OF THE COURT

We consider once again what are appropriate computer-related supervised release conditions for child pornography offenders. Appellant Randy Albertson pled guilty to one count of receiving child pornography in violation of 18 U.S.C. § 2252A(a)(2)(B). The District Court sentenced him to 60 months’ imprisonment (the minimum mandated) and 20 years’ supervised release with eight special conditions. On appeal, Albertson challenges the reasonableness of the 20-year term and three of the special conditions of his supervised release, including a restriction on internet access, mandatory computer monitoring, and a restriction on his association with minors. As we agree with Albertson only that a wholesale ban on his internet use is broader than necessary to accomplish the sentencing goals of 18 U.S.C. § 3553(a), we affirm the duration of the supervised release term and the association-with-minors restriction, vacate and remand the internet restriction, and remand the monitoring requirement for adaption to a more tailored internet restriction.

I. Background

Albertson’s problem with child pornography surfaced in 2005 when his wife discovered a pornographic image in his dresser drawer. Despite the family’s efforts to monitor his computer access thereafter, Albertson, a former prison guard, continued viewing child porn online. In addition, in 2006, Albertson’s wife (they are now divorced) reported to the local police that he had molested her teenaged daughter (his then-stepdaughter). ^[1] Consequently, the police searched the family computer. They found over 700 images of child porn, some of which featured pre-pubescent children.

Albertson was charged in a two-count superseding indictment with receipt and possession of child pornography, in viola[*194] tion of 18 U.S.C. § 2252A(a)(2)(B) and 18 U.S.C. § 2252A(a)(5)(B). He pled guilty to the receipt count and stipulated to 39 pornographic images. Receipt of child porn carries a mandatory minimum of five years’ imprisonment, 18 U.S.C. § 2252A(b)(l), and that minimum was the jail term imposed here. Five years’ supervised release is also required. 18 U.S.C. § 3583(k). In the plea, the parties agreed to a supervised release term of up to 25 years (with the parties able to argue at sentencing the appropriate term).

At his 2008 sentencing hearing, Albert-son himself argued to the Court as follows:

I found court cases — and this is through a Yoeker (phonetic) case that I found that involves two individuals, a Crandon and a Lloyd (phonetic), both received out of the Third Circuit here under five year sentences for supervised release, the Lloyd being, they’re — from what I’ve read out of their cases, you know, they don’t even compare to my case, my background, or anything that I have ever done as far as law enforcement is concerned. I ask that you, you know, review that and think about even less time than five years [of supervised release] because those two cases, Crandon and Lloyd, they got less than five out of this district. I ask for the same thing.

The Government requested the maximum supervised release term permitted by the plea agreement — 25 years. It stated the nature of the offense and the relevant conduct — that over 700 pornographic images were found (including prepubescent images) on Albertson’s computer, his wife’s discovery of an image, and his failure to abide by his family’s informal restrictions on his computer use.

After imposing the 60-month prison term, the Court decided on a 20-year term of supervised release with eight special conditions. Its primary considerations were the seriousness of the offense, the goal of “deter[ring Albertson’s] conduct in the future,” and the need “to protect the public.” On these bases, it found “that an extended term of supervised release is appropriate.”

Albertson appeals three of the special conditions. ^[2] He was: banned from “associating] with children under the age of 18 (with the exception of his children) except in the presence of an adult who has been approved by the Probation Officer” (Special Condition 4); barred from “us[ing] a computer with access to any ‘on-line computer service’ without the prior written approval of the probation officer” (Special Condition 5); and required to submit to an initial inspection, and subsequent inspections, of his computer and to allow the installation of monitoring or filtering software (Special Condition 7). The District Court did not discuss the details of these conditions nor did it provide specific reasons for imposing them. On appeal, Albertson argues they subject him to a greater deprivation of liberty than necessary. He relies principally on our decision in United States v. Miller, 594 F.3d 172 (3d Cir.2010). There, as here, we were confronted with a ban on internet use that was imposed on a child porn offender as a special condition of his supervised release. We concluded that the internet ban— which was imposed for life — was over-broad.

II. Waiver

In his opening brief, Albertson argues solely that the 20-year supervised release[*195] term is unreasonable. He neither raises nor refers to the conditions of his supervised release. It is only in his reply brief that he addresses those conditions and argues they are unlawful in light of Miller. Thus, we address a threshold question of waiver.

Albertson’s reason for his untimeliness was that our decision in Miller was filed one day after his opening brief. He informed us that it had not occurred to him to challenge his conditions prior to our analysis in that case. According to the Government, however, Albertson’s failure to challenge the conditions of his supervised release in his opening brief waived the argument. It urged us to strike the reply brief or, at least, consider the argument waived. Rather than strike the reply, we granted the Government’s request to file a surreply.

It is standard practice that an appellant must state all issues raised on appeal in the opening brief. See Fed. R.App. P. 28(a)(5); Third Cir. Local App. R. 28.1(a)(1). Indeed, it is essential to our review that the appellant properly present all issues in his opening brief. “It is well settled that an appellant’s failure to identify or argue an issue in his opening brief constitutes waiver of that issue on appeal.” United States v. Pelullo, 399 F.3d 197, 222 (3d Cir.2005); see, e.g., In re Surrick, 338 F.3d 224, 237 (3d Cir.2003); see also Inst, for Scientific Info., Inc. v. Gordon & Breach, Sci. Pubis., Inc., 931 F.2d 1002, 1011 (3d Cir.1991) (finding waiver because “[n]owhere in the ‘Statement of the Issues Presented’ or the ‘Argument’ section of plaintiffs appellate brief are [the district court’s] conclusions questioned”). For these reasons, “we usually refrain from addressing an argument or issue not properly raised and discussed in the appellate briefing.” Forestal Guarani S.A. v. Daros Int’l, Inc., 613 F.3d 395, 403 (3d Cir.2010) (Cowen, J., dissenting).

However, the rule does yield in “extraordinary circumstances.” See Simmons v. City of Phila., 947 F.2d 1042, 1065 (3d Cir.1991). Though our case law repeats the rule — waiver absent extraordinary cir cumstances — we have yet to flesh out the extraordinary circumstance exception. We find instructive an approach set out by one of our sister courts of appeals. In In re Kane, the First Circuit Court of Appeals acknowledged, as we do, that it lacked explicit standards for “what constitutes such extraordinary circumstances.” 254 F.3d 325, 331 (1st Cir.2001). It did, however, identify certain factors as “obvious” ones to consider: “whether there is some excuse for the 'failure to raise the issue in the opening brief; how far the opposing party would be prejudiced; and whether failing to consider the argument would lead to a miscarriage of justice or undermine confidence in the judicial system.” Id.

We agree and adopt these principles. Applied to the facts of Albertson’s case, we believe the balance weighs in favor of reviewing the merits of the challenge to his supervised release conditions.

With respect to the first factor, we appreciate that Albertson’s reason for failing to raise the issue in his opening brief is not compelling. As noted, his counsel stated at argument that, prior to Miller, he had not realized that a challenge to the conditions might succeed. This might be true as a subjective matter. Objectively, however, the basis for Miller already existed in a line of cases, discussed below, concerning computer-related conditions of supervised release that were imposed on child porn offenders. Thus, standing alone, the first factor does not cut against waiver.

[*196] However, the second two factors do weigh against waiver. The Government would suffer no prejudice in this case. Not only was it permitted to file a surreply, but it then failed to pursue meaningfully its waiver argument in the sur-reply. This indicates that it would not be prejudiced significantly by our review of the merits.

Lastly, the miscarriage of justice factor is “somewhat similar to the ‘plain error’ rule, which is applied in the context of appeals from criminal trials, and allows appellate courts to consider defects at the trial level even when the defendant has failed to lodge an appropriate objection.” Gambino v. Morris, 134 F.3d 156, 169 n. 12 (3d Cir.1998) (Roth, J., concurring) (citing Fed.R.Crim.P. 52(b)). In other words, we may consider an issue, despite the fact that it was improperly raised on appeal, if the District Court plainly erred in such a way as to affect the appellant’s substantial rights. See Fed.R.Crim.P. 52(b); United States v. Thielemann, 575 F.3d 265, 270 n. 9 (3d Cir.2009) (citing United States v. Olano, 507 U.S. 725, 732-34, 113 S.Ct. 1770, 123 L.Ed.2d 508 (1993)). “[E]ven where plain error exists [that affects substantial rights], our discretionary authority to order correction is to be guided by whether the error seriously affects the fairness, integrity or public reputation of judicial proceedings.” United States v. Knight, 266 F.3d 203, 207 (3d Cir.2001). If forced to ignore the challenge in this case, we turn a blind eye to supervised release conditions that are directly contrary to the line of cases, discussed below, governing the propriety of internet restrictions for child porn offenders in this Circuit. To do so would seriously “undermine confidence in the judicial system.” In re Kane, 254 F.3d at 331. Accordingly, on balance, the In re Kane factors we adopt tilt in favor of our review of the merits. ^[3]

III. The Special Conditions of Supervised Release

Because we conclude that Albertson’s arguments are not waived, we turn to the merits of his appeal. ^[4] A sentencing judge has wide discretion in imposing terms of supervised release. Subsections 3583(d)(1) and (2) authorize a sentencing court to impose conditions of supervised release provided they are reasonably related to the 18 U.S.C. § 3553(a) factors ^[5] and in[*197] volve “no greater deprivation of liberty than is reasonably necessary” to fulfill the purposes set out in that provision. See United States v. Pruden, 398 F.3d 241, 248 (3d Cir.2005). Accordingly, as the Sentencing Commission acknowledges, we review the reasonableness of a supervised release term against the § 3553(a) factors, recognizing that “the primary purpose of supervised release is to facilitate the integration of offenders back into the community rather than to punish them.” U.S. Sentencing Comm’n, Federal Offenders Sentenced to Supervised Release 8-9 (2010). Notably, in addition to the sentencing goals enumerated, § 3553(a) also requires parsimony — that “[t]he court impose a sentence sufficient, but not greater than necessary.”

A. The Internet Ban & the Monitoring Requirement

According to Albertson, the requirements that he not use a computer with any form of “online” access unless pre-approved by his probation officer, and the attendant monitoring of his computer usage, are disproportionate to his criminal history and offense characteristics. Thus, he argues, they are overbroad.

As noted above, we have recently dealt with a similar question in Miller, in which a child porn offender was sentenced to a lifetime term of supervised release that banned access to the internet. In ruling that the condition was overbroad, we reviewed our case law on “supervised release conditions restricting computer and internet usage for child pornography offenders.” 594 F.3d at 185; see Thielemann, 575 F.3d 265; United States v. Voelker, 489 F.3d 139 (3d Cir.2007); United States v. Freeman, 316 F.3d 386 (3d Cir.2003); United States v. Crandon, 173 F.3d 122 (3d Cir.1999); see also United States v. Maurer, 639 F.3d 72 (3d Cir.2011).

Taken together, the Miller-Crandon line of cases yields three themes. First, though not at issue here, a complete ban on the use of a computer and internet will rarely be sufficiently tailored to the § 3553(a) factors. Our opinion in Voelker illustrates this point. There, the defendant was banned from using all computers for life following a plea to receiving child pornography. We ruled that the “outright lifetime ban” on computers was “the antithesis of a narrowly tailored sanction, a greater deprivation of liberty than [was] reasonably necessary, and not reasonably related to the factors set forth in ... § 3583.” Miller, 594 F.3d at 185 (quoting Voelker, 489 F.3d at 144-45) (internal quotation marks omitted).

Second, moving along the spectrum of restrictiveness, a complete ban on internet access, except with prior approval of probation, may be permissibly imposed temporarily on those offenders who have used or have clearly demonstrated a willingness to use the internet as a direct instrument of physical harm. For instance, in Thielemann, Crandon, and Maurer the defendants used or demonstrated a willingness to use the internet to solicit, communicate with, or abuse a minor in conjunction with child porn offenses. In Thielemann, the defendant encouraged his online chat companion to abuse sexually a minor girl in[*198] front of a webcam. Moreover, Thielemann had several persons involved, and was the hub of the offensive conduct. See 575 F.3d at 268, 269 n. 4. Similarly, in Crandon the defendant used the internet to communicate, arrange to meet, and have sexual relations with a minor girl. In Maurer, the defendant expressed an interest in sexual contact with minors while using the internet in the attempt to arrange a sexual encounter. Thielemann and Crandon both used the internet to encourage or otherwise initiate the sexual abuse of a minor, as distinguished from solely accessing pornographic sites. Maurer clearly demonstrated a willingness to use the internet for these same purposes. We upheld, in their cases, conditions that proscribed all internet access for ten, three, and five years, respectively.

Finally, where the child porn offense does not involve a “live” component (that is, direct involvement or communication, including the attempt or demonstrated willingness to have direct involvement or communication, with a putative victim via the internet), the district courts should consider whether a tailored internet limitation is feasible. In Freeman, for example, the defendant pled to possessing and receiving child porn. There, as here, he had also molested children in the past. But absent the direct link between the internet and the abuse, we concluded that a blanket ban was overbroad. We noted that “[t]here is no need to cut off [a child porn offender’s] access to email or benign internet usage when a more focused restriction, limited to pornography sites and images, can be enforced by unannounced inspections of material stored on [the offender’s] hard drive or removable disks.” Miller, 594 F.3d at 186 (quoting Freeman, 316 F.3d at 392) (alteration in original) (internal quotation marks omitted).

Building from these themes, we set out in Miller three factors for assessing whether a supervised release condition is overbroad. We consider the scope of the condition first with respect to substantive breadth and second with respect to its duration. Miller, 594 F.3d at 187 & n. 9 (noting the similar factor-based approach adopted in United States v. Heckman, 592 F.3d 400, 405-08 (3d Cir.2010)). Third, we assess “the severity of the defendant’s criminal conduct and the facts underlying the conviction, with a particular focus on whether the defendant used a computer or the internet to solicit or otherwise personally endanger children.” Miller, 594 F.3d at 187.

Because we are mindful of the interplay between prison time and the term of supervised release, we now add it as a fourth factor. As a general matter, we agree with the Government that a district court may find it proper to impose a longer term of supervised release to follow a relatively shorter term of imprisonment. ^[6] In this context, we believe that the proportion of a supervised release restriction to the total period of restriction (including prison time) is also relevant to our review.

We now apply these factors to Albertson’s case. First, we note that the restrictiveness of the internet condition mirrors those in Thielemann and Crandon — no internet access unless preapproved by probation — a restriction that we recognize as sweepingly broad and, indeed, too broad unless the defendant has used the internet as an instrument of harm. See also Maurer, 639 F.3d at 84 (recognizing that, in addition to direct physical[*199] harm, an “expressed interest in minors, ... coupled with [a] demonstrated willingness to use the internet as a means for arranging sexual encounters, presents a tangible risk to children,” and thus supports as reasonable a total internet ban). As one of our sister courts of appeals has said, “such a ban renders modern life — in which, for example, the government strongly encourages taxpayers to file their returns electronically, where more and more commerce is conducted on-line, and where vast amounts of government information are communicated via website— exceptionally difficult.” United States v. Holm, 326 F.3d 872, 878 (7th Cir.2003). This aspect of the scope factor favors Albertson.

The duration of the supervised release term has an interesting twist. We recognize that his 20-year term is shorter than the lifetime bans imposed in both Miller and Voelker. 7 However, the length of the term must be considered relative to the defendant’s age. We do not believe that there is a meaningful distinction between the lifetime ban we struck down in Miller and the 20-year term imposed here. Miller was 60 at the time of his sentencing and Albertson was 42. Assuming an 80-year life expectancy, the combined duration for each is essentially the same. ^[8]

Turning to the conduct factor, the aforementioned cases show that a key consideration is whether the defendant used the internet “to actively contact a child and solicit sexual contact.” Miller, 594 F.3d at 188. Albertson did not. With this in mind, we repeat what we said in Miller: “While we do not intend to minimize the serious harm caused by possession of child pornography, [Albertson’s] use of the internet poses a danger that differs in both kind and degree from the conduct in Crandon and Thielemann.” Id. Thus, this factor favors Albertson.

However, Albertson’s relatively short incarceration sentence suggests that the length of the supervised release term is reasonable. Though we do not set a bright-line rule, we find no fault with Albertson’s sentence having a lengthy “tail” — that is, his term of supervised release comprises 80% of the total 25-year period of restriction on his liberty.

With these factors in context, we approve the 20-year term of supervised release in itself, but the internet restriction condition fails for overbreadth because it is too restrictive. If the District Court had a reason for imposing the type of internet restriction that we have typically reserved for offenders such as those in Crandon and Thielemann, it failed to state that reason. Accordingly, we can do little more than “flounder in the zone of speculation.” United States v. Loy, 191 F.3d 360, 371 (3d Cir.1999) (internal quotation marks and citation omitted). Thus we remand.

In contrast to the internet use restriction, Albertson’s computer monitoring condition — which requires him to submit his computer to inspections, and allow installation of monitoring or filtering software — would be generally acceptable if the internet restriction to which it applies is narrowly tailored and reasonable. Moreover, the condition’s requirement that Al[*200] bertson submit to initial and subsequent computer “examinations” finds statutory support in 18 U.S.C. § 3583(d)(3). ^[9] Hence the inspections, coupled with the required installation of monitoring or filtering software, are reasonable methods of enforcing a more targeted internet restriction. For these reasons, we discern no fault with similar monitoring conditions (that allow computer inspections and the installation of monitoring or filtering software) paired with a more tailored internet restriction.

To sum up, in a time where the daily necessities of life and work demand not only internet access but internet fluency, sentencing courts need to select the least restrictive alternative for achieving their sentencing purposes. In this case, the District Court may achieve that purpose through an internet prohibition and monitoring requirement to assure that Albert-son does not engage in offensive conduct. ^[10] We thus vacate both conditions and remand for that Court to fashion a “comprehensive, reasonably tailored scheme.” Miller, 594 F.3d at 188. ^[11]

B. The Associational Condition

Albertson claims there is no support in the record for imposing a prohibition on associating with minors under age 18 (except his family). While it is true that “[a] district court must state the reasons in open court for imposing a particular special condition so that the appellate court is not left to speculate about the reasons,” Miller, 594 F.3d at 184, (and that was not done here), we may “[nevertheless ... affirm the condition if our own review of the record reveals any viable basis for the restriction.” Id. at 189 (quoting Voelker, 489 F.3d at 144) (internal quotation marks omitted). At the time of his sentencing, Albertson had been charged with, among other things, indecent assault of his then-13- or 14-year-old step-daughter, and has since been convicted of that crime. There is thus ample support in the record for this condition. Its propriety is further corroborated by our approval of a nearly identical condition in Miller. 594 F.3d at 190. Though Al[*201] bertson’s condition does not explicitly allow for “casual encounters,” as did the one in Miller, we conclude that such a proviso is implicit in the condition: “At this point, it is well established that associational conditions do not extend to casual or chance meetings.” Id. at 191 n. 11 (internal quotation marks and citation omitted). Accordingly, we believe the association-with-minors condition is adequately supported by the record and consistent with the goals set forth in § 3553(a) as they are incorporated into § 3583(d). ^[12]

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We affirm the duration of the 20-year supervised release term and the challenged associational restriction. However, we vacate and remand for further proceedings on the internet restriction (Special Condition 5). We believe that a monitoring requirement is a reasonable means of enforcing a well-tailored internet restriction, but remand that condition (Special Condition 7) as well for any adjustments required in light of the re-fashioned internet restriction.